Haloalkyl alkoxymethyl ether compound, and methods of using the same to prepare 4,6,8,10,16-pentamethyldocosane and synthetic intermediate therefor

Abstract

To provide a comprehensive method for preparing compounds having 1,3-dimethyl skeletons, in particular, an efficient method for preparing 4,6,8,10,16-pentamethyldocosane.SOLUTION: The invention provides a method of preparing a haloalkyl alkoxymethyl ether compound represented by a general formula (1') in the figure.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a haloalkyl alkoxymethyl ether compound, and a method for producing 4,6,8,10,16-pentamethyldocosane and its synthetic intermediates using the same. [Background technology]

[0002] Compounds having a 1,3-dimethyl skeleton are widely known. For example, Antitrogus little boy 4,6,8,10,16-pentamethyldocosane, a cuticular hydrocarbon of Pearls from Prieska These include 2,4,6,8-tetramethylundecanol, 2,4,6,8,10-pentamethyltridecane, and 2,4,6,8,10,12,14,16-octamethylheptadecane, which are the sex pheromones of the Antitrogus little boy is a sugarcane pest in Australia, and organophosphate pesticides have been widely used to control this pest, but there are problems with residual pesticides, etc. Therefore, biological control methods that minimize the use of pesticides have been studied, and among these, control using cuticular hydrocarbons is one promising method (Non-Patent Document 1 below).

[0003] Antitrogus little boy Various compounds such as 4,6,8,10,16-pentamethyldocosane and 4,6,8,10,16,18-hexamethyldocosane are known as cuticular hydrocarbons of the insect.

[0004] For example, the synthesis of 4,6,8,10,16-pentamethyldocosane can be achieved by hydrogenating 2,4,6-trimethylphenol to synthesize 2,4,6-trimethylcyclohexanol, subjecting the resulting 2,4,6-trimethylcyclohexanol to Jones oxidation, followed by Baeyer-Villiger oxidation with 3-chloroperbenzoic acid (mCPBA), followed by ring-opening with sodium methoxide to synthesize 6-hydroxy-2,4-dimethylheptanoate. H-pyran is used to protect the tetrahydropyranyl group, and the ester of methyl 6-hydroxy-2,4-dimethylheptanoate is reduced with lithium aluminum hydride to give 2,4-dimethyl-6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-heptanol. The resulting 2,4-dimethyl-6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-heptanol is oxidized with pyridinium chlorochromate (PCC) in dichloromethane, then subjected to a Wittig reaction with ethyl 2-(triphenylphosphoranylidene)propanoate, the carbon-carbon double bond is hydrogenated with palladium carbon, the ester is reduced with lithium aluminum hydride, the hydroxyl group is iodized with triphenylphosphine, iodine, and imidazole, and then subjected to a coupling reaction with ethylmagnesium bromide. The tetrahydropyranyl group is deprotected with methanol under acidic conditions to synthesize 4,6,8-trimethyl-2-undecanol. Next, 4,6,8-trimethyl-2-undecanol is mesylated with triethylamine and methanesulfonyl chloride, and then reacted with sodium cyanide in dimethylsulfoxide (DMSO) to obtain 2,4,6,8-tetramethylundecanenitrile. Next, 2,4,6,8-tetramethylundecanenitrile is reacted with acetyl chloride in methanol to convert the nitrile group to a carboxylic acid, and then reduced with lithium aluminum hydride to synthesize 2,4,6,8-tetramethyl-1-undecanol. Next, 2,4,6,8-tetramethyl-1-undecanol is subjected to Swern oxidation of the hydroxyl group with triethylamine and oxalyl chloride in DMSO to synthesize 2,4,6,8-tetramethyl-1-undecanal. Next, 2,4,6,8-tetramethyl-1-undecanal and (5-methylundecylidene)triphenylphosphorane are subjected to a Wittig reaction, and the carbon-carbon double bond is reduced in the presence of a palladium carbon catalyst, resulting in a total of 19 steps and a production process that is 3.28% (Non-Patent Document 1 listed below). [Prior art documents] [Non-patent literature]

[0005] [Non-Patent Document 1] William Kitching et al.,J. Org. Chem.,2005,70,1808-1827. Summary of the Invention [Problem to be solved by the invention]

[0006] As mentioned above, Antitrogus little boy As surface hydrocarbons of the 4,6,8,10,16-pentamethyldocosane, various compounds such as 4,6,8,10,16,18-hexamethyldocosane are known. In this disclosure, the focus is on 4,6,8,10,16-pentamethyldocosane, but the present invention is not limited thereto. In the method for producing 4,6,8,10,16-pentamethyldocosane in Non-Patent Document 1, the method uses multiple steps of Jones oxidation, Baeyer-Villiger oxidation, PCC oxidation, and Swern oxidation, which are explosive, and lithium aluminum hydride and palladium carbon, which are flammable, in multiple steps. Furthermore, sodium cyanide, which is highly toxic, is used, making it unsuitable for industrial production. In addition, the method has many steps and a low yield, making it unsuitable for industrial production. In addition, the method for producing the 4,6,8,10,16-pentamethyldocosane described in Non-Patent Document 1 uses multiple steps of Jones oxidation, Baeyer-Villiger oxidation, PCC oxidation, and Swern oxidation, which are explosive, in multiple steps, and further uses lithium aluminum hydride and palladium carbon, which are flammable, in multiple steps, making it unsuitable for industrial production. In addition, the method for producing the 4,6,8,10,16-pentamethyldocosane described in Non-Patent Document 1 uses multiple steps of ... and further uses sodium cyanide, which is highly toxic. In addition, the method for producing the 4,6,8,10,16-pentamethyldocos Antitrogus little one Although it is possible to produce the surface hydrocarbons 4,6,8,10,16-pentamethyldocosane and 4,6,8,10,16,18-hexamethyldocosane, it is not possible to comprehensively synthesize various compounds having a 1,3-dimethyl skeleton other than these.

[0007] The present invention has been made in view of the above circumstances, and aims to provide a comprehensive method for producing compounds having a 1,3-dimethyl skeleton. Another aim of the present invention is to provide a novel synthetic intermediate useful for producing a compound having a 1,3-dimethyl skeleton, particularly 4,6,8,10,16-pentamethyldocosane, and a method for producing the synthetic intermediate. A further aim of the present invention is to provide an efficient method for producing 4,6,8,10,16-pentamethyldocosane, preferably an efficient and economical method, using the synthetic intermediate. [Means for solving the problem]

[0008] As a result of intensive research conducted by the present inventors to solve the above problems, they have found that a key intermediate capable of comprehensively synthesizing various compounds having a 1,3-dimethyl skeleton is a haloalkyl alkoxymethyl ether compound. The present inventors have further discovered a method for producing the haloalkyl alkoxymethyl ether compound at low cost and efficiently, and a method for producing the haloalkyl alkoxymethyl ether compound and a method for producing the same. Antitrogus little boy The present invention has been made by discovering a method for producing 4,6,8,10,16-pentamethyldocosane, a surface hydrocarbon compound of the sea urchin, in a short process. The above-mentioned production method has also been found to be suitable for industrial production.

[0009] According to a first aspect of the present invention, The following general formula (1): [ka] (In the formula, X 1 represents a halogen atom, and R 1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and n represents an integer of 2 to 7. A haloalkyl alkoxymethyl ether compound represented by the following general formula (2): [ka] (In the formula, M1 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 where Z 1 is a halogen atom or Z 2 represents Z 2 teeth, [ka] and R 1 and n are as defined above, and the wavy line indicates that the structure beyond it is omitted.) and converting the (2n+2)-alkoxymethoxyalkyl nucleophile (2) into a (2n+2)-alkoxymethoxyalkyl nucleophile represented by the following formula (3): [ka] By subjecting the compound to a nucleophilic addition reaction with propylene oxide represented by the following general formula (4): [ka] (In the formula, R 1 and n is as defined above. obtaining a hydroxyalkyl alkoxymethyl ether compound represented by the formula: The hydroxyalkyl alkoxymethyl ether compound (4) is halogenated to give the following general formula (1'): [ka] (In the formula, X 1 , R 1 and n is as defined above. obtaining a haloalkyl alkoxymethyl ether compound represented by the formula: The present invention provides a method for producing a haloalkyl alkoxymethyl ether compound (1'), comprising at least the steps of:

[0010] According to a second aspect of the present invention, there is provided a method for producing a haloalkyl alkoxymethyl ether compound (1':n+1=3) according to the first embodiment, wherein n is 2 in the haloalkyl alkoxymethyl ether compounds (1) and (1').

[0011] According to a third aspect of the present invention, A method for producing a haloalkyl alkoxymethyl ether compound (1':n+1=3), for example, a method for producing a haloalkyl alkoxymethyl ether compound (1':n+1=3) according to the first embodiment described above, or another method for producing a haloalkyl alkoxymethyl ether compound (1':n+1=3), for example, a method for producing a haloalkyl alkoxymethyl ether compound (1':n+1=3) according to any one of Examples 5 and 6 described herein; The haloalkyl alkoxymethyl ether compound (1':n+1=3) is reacted with a compound represented by the following general formula (2:n=3): [ka] (In the formula, M 1 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 where Z 1 represents a halogen atom or an 8-alkoxymethoxy-1,3,5-trimethyloctyl group, and R 1 is as defined above.) The 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile (2:n=3) is converted into an 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile represented by the following general formula (5): [ka] (In the formula, X 2 represents a halogen atom.) By subjecting the compound represented by the following general formula (6): [ka] (In the formula, R1 is as defined above.) obtaining a 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound represented by the formula: The 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) is subjected to a dealkoxymethylation reaction to obtain a compound represented by the following formula (7): [ka] obtaining 4,6,8,10-tetramethyltridecanol represented by the formula: The 4,6,8,10-tetramethyltridecanol (7) is subjected to a halogenation reaction to obtain a compound represented by the following general formula (8): [ka] (In the formula, X 3 represents a halogen atom.) obtaining a 1-halo-4,6,8,10-tetramethyltridecane compound (8) represented by the formula: The 1-halo-4,6,8,10-tetramethyltridecane compound (8) is reacted with a compound represented by the following general formula (9): [ka] (In the formula, M 2 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 where Z 1 represents a halogen atom or a 4,6,8,10-tetramethyltridecyl group. The 4,6,8,10-tetramethyltridecyl nucleophile (9) is converted into a 4,6,8,10-tetramethyltridecyl nucleophile represented by the following general formula (10): [ka] (In the formula, X 4 represents a halogen atom.) By subjecting the compound represented by the following general formula (11): [ka] and obtaining 4,6,8,10,16-pentamethyldocosane represented by the formula: The present invention provides a method for producing 4,6,8,10,16-pentamethyldocosane (11), comprising at least

[0012] According to a fourth aspect of the present invention, The following general formula (1:n=3): [ka] (In the formula, X 1 represents a halogen atom, and R 1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group. A haloalkyl alkoxymethyl ether compound represented by the following general formula (2: n = 3): [ka] (In the formula, M 1 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 where Z 1 represents a halogen atom or an 8-alkoxymethoxy-1,3,5-trimethyloctyl group, and R 1 is as defined above.) The 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile (2:n=3) is converted into an 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile represented by the following general formula (5): [ka] (In the formula, X 2 represents a halogen atom.) By subjecting the compound represented by the following general formula (6): [ka] (In the formula, R 1 is as defined above.) obtaining a 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound represented by the formula: The 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) is subjected to a dealkoxymethylation reaction to obtain a compound represented by the following formula (7): [ka] obtaining 4,6,8,10-tetramethyltridecanol represented by the formula: The 4,6,8,10-tetramethyltridecanol (7) is subjected to a halogenation reaction to obtain a compound represented by the following general formula (8): [ka] (In the formula, X 3 represents a halogen atom.) obtaining a 1-halo-4,6,8,10-tetramethyltridecane compound (8) represented by the formula: The 1-halo-4,6,8,10-tetramethyltridecane compound (8) is reacted with a compound represented by the following general formula (9): [ka] (In the formula, M 2 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 where Z 1 represents a halogen atom or a 4,6,8,10-tetramethyltridecyl group. The 4,6,8,10-tetramethyltridecyl nucleophile (9) is converted into a 4,6,8,10-tetramethyltridecyl nucleophile represented by the following general formula (10): [ka] (In the formula, X 4 represents a halogen atom.) By subjecting the compound represented by the following general formula (11): [ka] and obtaining 4,6,8,10,16-pentamethyldocosane represented by the formula: The present invention provides a method for producing 4,6,8,10,16-pentamethyldocosane (11), comprising at least

[0013] According to a fifth aspect of the present invention, there is provided a compound represented by the following general formula (1'): [ka] (In the formula, X 1 represents a halogen atom, and R 1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and n represents an integer of 2 to 7. The present invention provides a haloalkyl alkoxymethyl ether compound represented by the formula: Effect of the Invention

[0014] According to the present invention, it is possible to produce a haloalkyl alkoxymethyl ether compound, which is a building block capable of comprehensively synthesizing compounds having a 1,3-dimethyl skeleton. In addition, by using the haloalkyl alkoxymethyl ether compound as a key intermediate, it is possible to efficiently produce 4,6,8,10,16-pentamethyldocosane, a compound having a 1,3-dimethyl skeleton, in a short process with little environmental impact. This production method is also economical. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] I. Haloalkyl alkoxymethyl ether compounds represented by the following general formulas (1) and (1') First, the haloalkyl alkoxymethyl ether compounds (1) and (1') will be described.

[0016] [ka] In each of the above general formulas (1) and (1′), X 1 represents a halogen atom. Halogen atom X 1 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of reactivity, a chlorine atom and a bromine atom are preferred, and a chlorine atom is particularly preferred. In each of the above general formulas (1) and (1′), R 1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, preferably 1 to 4 carbon atoms, or a phenyl group. The n-alkyl group includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a nonyl group. n is an integer of 1 to 7. Depending on the value of n, 1 to 7, compound (1) may be compound (1:n=1), compound (1:n=2), compound (1:n=3), compound (1:n=4), compound (1:n=5), compound (1:n=6), or compound (1:n=7) (hereinafter, the cases where n is 1 to 7 will be collectively referred to as compound (1:n=1 to 7)). Similarly, compound (1') may be compound (1':n+1=2), compound (1':n+1=3), compound (1':n+1=4), compound (1':n+1=5), compound (1':n+1=6), compound (1':n+1=7) and compound (1':n'+1=8) depending on the value of n, 1 to 7 (hereinafter, the cases where n is 1 to 7 are collectively referred to as compound (1':n+1=2 to 8)). In this specification, the target compound of the present invention focuses on haloalkyl alkoxymethyl ether compounds where n is an integer of 2 to 7, preferably 2 to 6. Therefore, in compound (1), the cases where n is 2 to 7 are collectively referred to as compound (1:n=2 to 7), and in compound (1'), the cases where n is 2 to 7 are collectively referred to as compound (1':n+1=3 to 8).

[0017] Specific examples of the haloalkyl alkoxymethyl ether compounds (1) and (1') include the following compounds: 4-Chloropentyl methoxymethyl ether, 4-bromopentyl methoxymethyl ether, 4-iodopentyl methoxymethyl ether, 4-chloropentyl ethoxymethyl ether, 4-bromopentyl ethoxymethyl ether, 4-iodopentyl ethoxymethyl ether, 4-chloropentyl propyloxymethyl ether, 4-bromopentyl propyloxymethyl ether, 4-iodopentyl propyloxymethyl ether, 4-chloropentyl butyloxymethyl ether, 4-bromopentyl butyloxymethyl ether, 4-iodopentyl butyloxymethyl ether, 4-chloropentyl pentyloxymethyl ether, 4-bromopentyl pentyloxymethyl ether, 4-iodopentyl pentyloxymethyl ether, 4-chloropentyl hexyloxymethyl ether, 4-bromopentyl hexyloxymethyl ether, 4-iodopentyl hexyloxymethyl ether, 4-halopentyl alkoxymethyl ether compounds (1:n=1) such as 4-halopentyloxymethyl ether, 4-chloropentyl heptyloxymethyl ether, 4-bromopentyl heptyloxymethyl ether, 4-iodopentyl heptyloxymethyl ether, 4-chloropentyl octyloxymethyl ether, 4-bromopentyl octyloxymethyl ether, 4-iodopentyl octyloxymethyl ether, 4-chloropentyl nonyloxymethyl ether, 4-bromopentyl nonyloxymethyl ether, 4-iodopentyl nonyloxymethyl ether, 4-chloropentyl decyloxymethyl ether, 4-bromopentyl decyloxymethyl ether, 4-iodopentyl decyloxymethyl ether, 4-chloropentyl benzyloxymethyl ether, 4-bromopentyl benzyloxymethyl ether and 4-iodopentyl benzyloxymethyl ether; 6-chloro-4-methylheptyl methoxymethyl ether, 6-bromo-4-methylheptyl methoxymethyl ether, 6-iodo-4-methylheptyl methoxymethyl ether, 6-chloro-4-methylheptyl ethoxymethyl ether, 6-bromo-4-methylheptyl ethoxymethyl ether, 6-iodo-4-methylheptyl ethoxymethyl ether, 6-chloro-4-methylheptyl propyloxymethyl ether, 6-bromo-4-methylheptyl propyloxymethyl ether, 6-iodo 6-iodo-4-methylheptyl propyloxymethyl ether, 6-chloro-4-methylheptyl butyloxymethyl ether, 6-bromo-4-methylheptyl butyloxymethyl ether, 6-iodo-4-methylheptyl butyloxymethyl ether, 6-chloro-4-methylheptyl pentyloxymethyl ether, 6-bromo-4-methylheptyl pentyloxymethyl ether, 6-iodo-4-methylheptyl pentyloxymethyl ether, 6-chloro-4-methylheptyl hexyloxymethyl ether methyl ether, 6-bromo-4-methylheptyl hexyloxymethyl ether, 6-iodo-4-methylheptyl hexyloxymethyl ether, 6-chloro-4-methylheptyl heptyloxymethyl ether, 6-bromo-4-methylheptyl heptyloxymethyl ether, 6-iodo-4-methylheptyl heptyloxymethyl ether, 6-chloro-4-methylheptyl octyloxymethyl ether, 6-bromo-4-methylheptyl octyloxymethyl ether, 6-iodo-4-methylheptyl octyloxymethyl ether, 6-iodo-4- methylheptyl octyloxymethyl ether, 6-chloro-4-methylheptyl nonyloxymethyl ether, 6-bromo-4-methylheptyl nonyloxymethyl ether, 6-iodo-4-methylheptyl nonyloxymethyl ether, 6-chloro-4-methylheptyl decyloxymethyl ether, 6-bromo-4-methylheptyl decyloxymethyl ether, 6-iodo-4-methylheptyl decyloxymethyl ether, 6-chloro-4-methylheptyl benzyloxymethyl ether,6-halo-4-methylheptyl alkoxymethyl ether compounds ((1:n=2) or (1':n+1=2)) such as 6-bromo-4-methylheptyl benzyloxymethyl ether and 6-iodo-4-methylheptyl benzyloxymethyl ether; 8-Chloro-4,6-dimethylnonyl methoxymethyl ether, 8-bromo-4,6-dimethylnonyl methoxymethyl ether, 8-iodo-4,6-dimethylnonyl methoxymethyl ether, 8-chloro-4,6-dimethylnonyl ethoxymethyl ether, 8-bromo-4,6-dimethylnonyl ethoxymethyl ether, 8-iodo-4,6-dimethylnonyl ethoxymethyl ether, 8-chloro-4,6-dimethylnonyl propyloxymethyl ether, 8-bromo-4,6-dimethylnonyl propyloxymethyl ether ether, 8-iodo-4,6-dimethylnonyl propyloxymethyl ether, 8-chloro-4,6-dimethylnonyl butyloxymethyl ether, 8-bromo-4,6-dimethylnonyl butyloxymethyl ether, 8-iodo-4,6-dimethylnonyl butyloxymethyl ether, 8-chloro-4,6-dimethylnonyl pentyloxymethyl ether, 8-bromo-4,6-dimethylnonyl pentyloxymethyl ether, 8-iodo-4,6-dimethylnonyl pentyloxymethyl ether, 8-chloro-4,6-dimethylnonyl pentyloxymethyl ether Methylnonyl hexyloxymethyl ether, 8-bromo-4,6-dimethylnonyl hexyloxymethyl ether, 8-iodo-4,6-dimethylnonyl hexyloxymethyl ether, 8-chloro-4,6-dimethylnonyl heptyloxymethyl ether, 8-bromo-4,6-dimethylnonyl heptyloxymethyl ether, 8-iodo-4,6-dimethylnonyl heptyloxymethyl ether, 8-chloro-4,6-dimethylnonyl octyloxymethyl ether, 8-bromo-4,6-dimethylnonyl octyloxymethyl ether oxymethyl ether, 8-iodo-4,6-dimethylnonyl octyloxymethyl ether, 8-chloro-4,6-dimethylnonyl nonyloxymethyl ether, 8-bromo-4,6-dimethylnonyl nonyloxymethyl ether, 8-iodo-4,6-dimethylnonyl nonyloxymethyl ether, 8-chloro-4,6-dimethylnonyl decyloxymethyl ether, 8-bromo-4,6-dimethylnonyl decyloxymethyl ether, 8-iodo-4,6-dimethylnonyl decyloxymethyl ether, 8-chloro-4,6-dimethylnonyl decyloxymethyl ether,8-Halo-4,6-dimethylnonyl alkoxymethyl ether compounds ((1:n=3) or (1':n+1=3)), such as 6-dimethylnonyl benzyloxymethyl ether, 8-bromo-4,6-dimethylnonyl benzyloxymethyl ether and 8-iodo-4,6-dimethylnonyl benzyloxymethyl ether; and 10-Chloro-4,6,8-trimethylundecyl methoxymethyl ether, 10-bromo-4,6,8-trimethylundecyl methoxymethyl ether, 10-iodo-4,6,8-trimethylundecyl methoxymethyl ether, 10-chloro-4,6,8-trimethylundecyl ethoxymethyl ether, 10-bromo-4,6,8-trimethylundecyl ethoxymethyl ether, 10-iodo-4,6,8-trimethylundecyl ethoxymethyl ether, 10-chloro-4,6,8-trimethylundecyl propionate propyloxymethyl ether, 10-bromo-4,6,8-trimethylundecyl propyloxymethyl ether, 10-iodo-4,6,8-trimethylundecyl propyloxymethyl ether, 10-chloro-4,6,8-trimethylundecyl butyloxymethyl ether, 10-bromo-4,6,8-trimethylundecyl butyloxymethyl ether, 10-iodo-4,6,8-trimethylundecyl butyloxymethyl ether, 10-chloro-4,6,8-trimethylundecyl pentyloxymethyl ether ether, 10-bromo-4,6,8-trimethylundecyl pentyloxymethyl ether, 10-iodo-4,6,8-trimethylundecyl pentyloxymethyl ether, 10-chloro-4,6,8-trimethylundecyl hexyloxymethyl ether, 10-bromo-4,6,8-trimethylundecyl hexyloxymethyl ether, 10-iodo-4,6,8-trimethylundecyl hexyloxymethyl ether, 10-chloro-4,6,8-trimethylundecyl heptyloxymethyl ether, 10 -Bromo-4,6,8-trimethylundecyl heptyloxymethyl ether, 10-iodo-4,6,8-trimethylundecyl heptyloxymethyl ether, 10-chloro-4,6,8-trimethylundecyl octyloxymethyl ether, 10-bromo-4,6,8-trimethylundecyl octyloxymethyl ether, 10-iodo-4,6,8-trimethylundecyl octyloxymethyl ether, 10-chloro-4,6,8-trimethylundecyl nonyloxymethyl ether, 10-bromo-4,6,10-halo-4,6,8-trimethylundecyl alkoxymethyl ether compounds such as 8-trimethylundecyl nonyloxymethyl ether, 10-iodo-4,6,8-trimethylundecyl nonyloxymethyl ether, 10-chloro-4,6,8-trimethylundecyl decyloxymethyl ether, 10-bromo-4,6,8-trimethylundecyl decyloxymethyl ether, 10-iodo-4,6,8-trimethylundecyl decyloxymethyl ether, 10-chloro-4,6,8-trimethylundecyl benzyloxymethyl ether, 10-bromo-4,6,8-trimethylundecyl benzyloxymethyl ether, and 10-iodo-4,6,8-trimethylundecyl benzyloxymethyl ether ((1:n=4) or (1':n+1=4)); 12-chloro-4,6,8,10-tetramethyltridecyl methoxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl methoxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl methoxymethyl ether, 12-chloro-4,6,8,10-tetramethyltridecyl ethoxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl ethoxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl ethoxymethyl ether, 12-chloro 12-bromo-4,6,8,10-tetramethyltridecyl propyloxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl propyloxymethyl ether, 12-chloro-4,6,8,10-tetramethyltridecyl butyloxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl butyloxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl butyloxymethyl ether 12-chloro-4,6,8,10-tetramethyltridecyl pentyloxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl pentyloxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl pentyloxymethyl ether, 12-chloro-4,6,8,10-tetramethyltridecyl hexyloxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl hexyloxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl hexyloxymethyl ether, 12-chloro-4,6,8,10-tetramethyltridecyl heptyloxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl heptyloxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl heptyloxymethyl ether, 12-chloro-4,6,8,10-tetramethyltridecyl octyloxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl octyloxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl octyloxymethyl ether, 12-chloro-4,6,8,10-tetramethyltridecyl nonyloxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl nonyloxymethyl ether, 12-iodo-4,6,8,10-tetramethyltridecyl nonyloxymethyl ether, 12-chloro-4,6,8,10-tetramethyltridecyl decyloxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl decyloxymethyl ether 12-halo-4,6,8,10-tetramethyltridecyl alkoxymethyl ether compounds ((1:n=5) or (1':n+1=5)) such as 12-iodo-4,6,8,10-tetramethyltridecyl decyloxymethyl ether, 12-chloro-4,6,8,10-tetramethyltridecyl benzyloxymethyl ether, 12-bromo-4,6,8,10-tetramethyltridecyl benzyloxymethyl ether and 12-iodo-4,6,8,10-tetramethyltridecyl benzyloxymethyl ether; 14-Chloro-4,6,8,10,12-pentamethylpentadecyl methoxymethyl ether, 14-Bromo-4,6,8,10,12-pentamethylpentadecyl methoxymethyl ether, 14-Iodo-4,6,8,10,12-pentamethylpentadecyl methoxymethyl ether, 14-Chloro-4,6,8,10,12-pentamethylpentadecyl ethoxymethyl ether, 14-Bromo-4,6,8,10,12-pentamethylpentadecyl ethoxymethyl ether, 14-Iodo-4,6,8,10,12-pentamethylpentadecyl Pentadecyl ethoxymethyl ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl propyloxymethyl ether, 14-bromo-4,6,8,10,12-pentamethylpentadecyl propyloxymethyl ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl propyloxymethyl ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl butyloxymethyl ether, 14-bromo-4,6,8,10,12-pentamethylpentadecyl butyloxymethyl ether ethyl ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl butyloxymethyl ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl pentyloxymethyl ether, 14-bromo-4,6,8,10,12-pentamethylpentadecyl pentyloxymethyl ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl pentyloxymethyl ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl hexyloxymethyl ether, 14- Bromo-4,6,8,10,12-pentamethylpentadecyl hexyloxymethyl ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl hexyloxymethyl ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl heptyloxymethyl ether, 14-bromo-4,6,8,10,12-pentamethylpentadecyl heptyloxymethyl ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl heptyloxymethyl ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl octyloxymethyl ether, 14-bromo-4,6,8,10,12-pentamethylpentadecyl octyloxymethyl ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl octyloxymethyl ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl nonyloxymethyl ether, 14-bromo-4,6,8,10,12-pentamethylpentadecyl nonyloxymethyl ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl nonyloxymethyl ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl decyloxymethyl ether ether, 14-bromo-4,6,8,10,12-pentamethylpentadecyl=decyloxymethyl=ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl=decyloxymethyl=ether, 14-chloro-4,6,8,10,12-pentamethylpentadecyl=benzyloxymethyl=ether, 14-bromo-4,6,8,10,12-pentamethylpentadecyl=benzyloxymethyl=ether, 14-iodo-4,6,8,10,12-pentamethylpentadecyl=benzyloxymethyl=ether, and other 14-halo-4,6,8,10,12-pentamethylpentadecyl=alkoxymethyl=ether compounds ((1:n=6) or (1':n+1=6)); 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl methoxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl methoxymethyl ether, 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl methoxymethyl ether, 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl ethoxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl ethoxymethyl ether, 1 7-Iodo-4,6,8,10,12,14-hexamethylheptadecyl ethoxymethyl ether, 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl propyloxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl propyloxymethyl ether, 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl propyloxymethyl ether, 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl butyloxymethyl ether 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl butyloxymethyl ether, 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl butyloxymethyl ether, 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl pentyloxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl pentyloxymethyl ether, 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl pentyloxymethyl ether 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl hexyloxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl hexyloxymethyl ether, 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl hexyloxymethyl ether, 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl heptyloxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl heptyloxymethyl ether14-Hexamethylheptadecyl heptyloxymethyl ether, 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl heptyloxymethyl ether, 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl octyloxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl octyloxymethyl ether, 17-iodo -4,6,8,10,12,14-Hexamethylheptadecyl octyloxymethyl ether, 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl nonyloxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl nonyloxymethyl ether, 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl nonyloxymethyl ether 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl decyloxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl decyloxymethyl ether, 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl decyloxymethyl ether, 17-chloro-4,6,8,10,12,14-hexamethylheptadecyl benzoate 17-halo-4,6,8,10,12,14-hexamethylheptadecyl benzyloxymethyl ether, 17-bromo-4,6,8,10,12,14-hexamethylheptadecyl benzyloxymethyl ether and 17-iodo-4,6,8,10,12,14-hexamethylheptadecyl benzyloxymethyl ether ((1:n=7) or (1':n+1=7)); 19-Chloro-4,6,8,10,12,14,16-heptamethylnonadecyl methoxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl methoxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl methoxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl ethoxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl ethoxymethyl ether , 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl ethoxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl propyloxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl propyloxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl propyloxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl butyl 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl butyloxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl butyloxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl pentyloxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl pentyloxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl pentyloxymethyl ether Methylnonadecyl pentyloxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl hexyloxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl hexyloxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl hexyloxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl heptyloxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl heptyloxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl heptyloxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl octyloxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl octyloxymethyl ether 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl octyloxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl nonyloxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl nonyloxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl nonyloxymethyl ether Nonyloxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl decyloxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl decyloxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl decyloxymethyl ether, 19-chloro-4,6,8,10,12,14,16-heptamethylnonadecyl decyloxymethyl ether 19-halo-4,6,8,10,12,14,16-heptamethylnonadecyl benzyloxymethyl ether, 19-bromo-4,6,8,10,12,14,16-heptamethylnonadecyl benzyloxymethyl ether, 19-iodo-4,6,8,10,12,14,16-heptamethylnonadecyl benzyloxymethyl ether, and other 19-halo-4,6,8,10,12,14,16-heptamethylnonadecyl alkoxymethyl ether compounds (1':n+1=8). The method for producing the haloalkyl alkoxymethyl ether compounds (1) and (1') is not particularly limited, but they can be obtained, for example, by the methods described in Sections II and III and Examples 2, 4, 5, 6 and 11 below.

[0018] II. Preparation of haloalkyl alkoxymethyl ether compounds (1':n+1=2-8) A haloalkyl alkoxymethyl ether compound represented by the following general formula (1': n+1 = 2 to 8) is produced from a haloalkyl alkoxymethyl ether compound (1: n = 1 to 7) according to the production method shown in the following chemical reaction formula.

[0019] [ka]

[0020] That is, haloalkyl alkoxymethyl ether compound (1':n+1=2-8) can be prepared by converting haloalkyl alkoxymethyl ether compound (1:n=1-7) to (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2), and then subjecting the (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) to a nucleophilic addition reaction with propylene oxide (3) to produce hydroxyalkyl alkoxymethyl ether compound (4). Next, the hydroxyalkyl alkoxymethyl ether compound (4) can be subjected to a halogenation reaction.

[0021] (i) (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) and its preparation method (a) The above (2n+2)-alkoxymethoxyalkyl nucleophile (2) is explained below. The (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) is represented by the following general formula (2). [ka] M in the above general formula (2) 1 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 where Z 1 is a halogen atom or Z 2 represents Z 2 teeth, [ka] and R1 and n are as defined in the above general formulas (1) and (1'), and the wavy line indicates that the structure following it is omitted. n is as defined above and is an integer of 1 to 7. A halogen atom Z 1 Examples of the aryl group include a chlorine atom, a bromine atom, and an iodine atom. (2n+2)-Alkoxymethoxyalkyl nucleophiles (2:M 1 =MgZ 1 ) is a Grignard reagent.

[0022] Specific examples of the (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) include (2n+2)-alkoxymethoxyalkyllithium; (2n+2)-alkoxymethoxyalkylmagnesium halide reagents (M) such as (2n+2)-alkoxymethoxyalkylmagnesium chloride, (2n+2)-alkoxymethoxyalkylmagnesium bromide, and (2n+2)-alkoxymethoxyalkylmagnesium iodide. 1 =MgZ 1 (The above are Grignard reagents); Bis[(2n+2)-alkoxymethoxyalkyl]cuprate (M 1 =CuZ 1 and Gilman reagents such as lithium bis[(2n+2)-alkoxymethoxyalkyl]cuprate (M 1 =CuLiZ 1 In the case where the alkoxy group is a methoxy group, a Gilman reagent is preferably used. From the viewpoint of reactivity, a Grignard reagent such as a (2n+2)-alkoxymethoxyalkylmagnesium halide reagent is preferable. The (2n+2)-alkoxymethoxyalkyl nucleophile (2) can be used not only to prepare the haloalkyl alkoxymethyl ether compound (1'), but also to prepare 4,6,8,10,16-pentamethyldocosane in the case of the 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile (2: n=3), as shown in Section IV below, where n is 3.

[0023] (b) Next, a method for producing the above (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) will be described below. The (2n+2)-alkoxymethoxyalkyl nucleophiles (2) can be prepared using the haloalkyl alkoxymethyl ether compounds (1) described above. For example, the (2n+2)-alkoxymethoxyalkyl nucleophile (2) is 1 MgZ 1 In the case of (2n+2)-alkoxymethoxyalkylmagnesium=halide reagent (2:M 1 =MgZ 1 ) will be described as an example of a method for producing the same. (2n+2)-Alkoxymethoxyalkylmagnesium = halide reagent (2:M 1 =MgZ 1 ) can be prepared, for example, by reacting the above haloalkyl alkoxymethyl ether compound (1) with magnesium in a solvent, as shown in the following chemical reaction scheme.

[0024] [ka]

[0025] The amount of magnesium used is preferably 1.0 to 2.0 gram atoms per mole of the haloalkyl alkoxymethyl ether compound (1) from the viewpoint of completing the reaction.

[0026] Examples of the solvent include general solvents, for example, ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; and hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene. From the viewpoint of the reaction rate of the production of the Grignard reagent, preferred are hydrocarbon solvents such as toluene and xylene; and ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran, and more preferred are tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mole of the haloalkyl alkoxymethyl ether compound (1) from the viewpoint of reactivity.

[0027] The reaction temperature varies depending on the solvent used, but is preferably 30 to 120° C. from the viewpoint of reactivity. The reaction time varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0028] (ii) Hydroxyalkyl alkoxymethyl ether compound (4) and its production method (a) The hydroxyalkyl alkoxymethyl ether compound (4) is explained below. The hydroxyalkyl alkoxymethyl ether compound (4) is represented by the following general formula (4). [ka] In the above general formula (4), R 1 and n is as defined in general formulae (1) and (1').

[0029] Specific examples of the hydroxyalkyl alkoxymethyl ether compound (4) include the following compounds: 6-hydroxy-4-methylheptyl alkoxymethyl ether compounds (n=1) such as 6-hydroxy-4-methylheptyl methoxymethyl ether, 6-hydroxy-4-methylheptyl ethoxymethyl ether, 6-hydroxy-4-methylheptyl propyloxymethyl ether, 6-hydroxy-4-methylheptyl butyloxymethyl ether, 6-hydroxy-4-methylheptyl pentyloxymethyl ether, 6-hydroxy-4-methylheptyl hexyloxymethyl ether, 6-hydroxy-4-methylheptyl heptyloxymethyl ether, 6-hydroxy-4-methylheptyl octyloxymethyl ether, 6-hydroxy-4-methylheptyl nonyloxymethyl ether, 6-hydroxy-4-methylheptyl decyloxymethyl ether and 6-hydroxy-4-methylheptyl benzyloxymethyl ether; 8-hydroxy-4,6-dimethylnonyl alkoxymethyl ether compounds (n=2) such as 8-hydroxy-4,6-dimethylnonyl methoxymethyl ether, 8-hydroxy-4,6-dimethylnonyl ethoxymethyl ether, 8-hydroxy-4,6-dimethylnonyl propyloxymethyl ether, 8-hydroxy-4,6-dimethylnonyl butyloxymethyl ether, 8-hydroxy-4,6-dimethylnonyl pentyloxymethyl ether, 8-hydroxy-4,6-dimethylnonyl hexyloxymethyl ether, 8-hydroxy-4,6-dimethylnonyl heptyloxymethyl ether, 8-hydroxy-4,6-dimethylnonyl octyloxymethyl ether, 8-hydroxy-4,6-dimethylnonyl nonyloxymethyl ether, 8-hydroxy-4,6-dimethylnonyl decyloxymethyl ether and 8-hydroxy-4,6-dimethylnonyl benzyloxymethyl ether; 10-hydroxy-4,6,8-trimethylundecyl methoxymethyl ether, 10-hydroxy-4,6,8-trimethylundecyl ethoxymethyl ether, 10-hydroxy-4,6,8-trimethylundecyl propyloxymethyl ether, 10-hydroxy-4,6,8-trimethylundecyl butyloxymethyl ether, 10-hydroxy-4,6,8-trimethylundecyl pentyloxymethyl ether, 10-hydroxy-4,6,8-trimethylundecyl hexyloxymethyl ether, 10-hydroxy 10-hydroxy-4,6,8-trimethylundecyl alkoxymethyl ether compounds (n=3) such as 10-hydroxy-4,6,8-trimethylundecyl heptyloxymethyl ether, 10-hydroxy-4,6,8-trimethylundecyl octyloxymethyl ether, 10-hydroxy-4,6,8-trimethylundecyl nonyloxymethyl ether, 10-hydroxy-4,6,8-trimethylundecyl decyloxymethyl ether and 10-hydroxy-4,6,8-trimethylundecyl benzyloxymethyl ether; 12-Hydroxy-4,6,8,10-tetramethyltridecyl methoxymethyl ether, 12-Hydroxy-4,6,8,10-tetramethyltridecyl ethoxymethyl ether, 12-Hydroxy-4,6,8,10-tetramethyltridecyl propyloxymethyl ether, 12-Hydroxy-4,6,8,10-tetramethyltridecyl butyloxymethyl ether, 12-Hydroxy-4,6,8,10-tetramethyltridecyl pentyloxymethyl ether, 12-Hydroxy-4,6,8,10-tetramethyltridecyl hexyloxymethyl ether, 12-Hydroxy 12-hydroxy-4,6,8,10-tetramethyltridecyl alkoxymethyl ether compounds (n=4) such as 12-hydroxy-4,6,8,10-tetramethyltridecyl heptyloxymethyl ether, 12-hydroxy-4,6,8,10-tetramethyltridecyl octyloxymethyl ether, 12-hydroxy-4,6,8,10-tetramethyltridecyl nonyloxymethyl ether, 12-hydroxy-4,6,8,10-tetramethyltridecyl decyloxymethyl ether and 12-hydroxy-4,6,8,10-tetramethyltridecyl benzyloxymethyl ether; 14-Hydroxy-4,6,8,10,12-pentamethylpentadecyl methoxymethyl ether, 14-Hydroxy-4,6,8,10,12-pentamethylpentadecyl ethoxymethyl ether, 14-Hydroxy-4,6,8,10,12-pentamethylpentadecyl propyloxymethyl ether, 14-Hydroxy-4,6,8,10,12-pentamethylpentadecyl butyloxymethyl ether, 14-Hydroxy-4,6,8,10,12-pentamethylpentadecyl pentyloxymethyl ether, 14-Hydroxy-4,6,8,10,12-pentamethylpentadecyl hexyloxymethyl ether, 14-Hydroxy 14-hydroxy-4,6,8,10,12-pentamethylpentadecyl alkoxymethyl ether compounds (n=5) such as 14-hydroxy-4,6,8,10,12-pentamethylpentadecyl heptyloxymethyl ether, 14-hydroxy-4,6,8,10,12-pentamethylpentadecyl octyloxymethyl ether, 14-hydroxy-4,6,8,10,12-pentamethylpentadecyl nonyloxymethyl ether, 14-hydroxy-4,6,8,10,12-pentamethylpentadecyl decyloxymethyl ether and 14-hydroxy-4,6,8,10,12-pentamethylpentadecyl benzyloxymethyl ether; 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl methoxymethyl ether, 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl ethoxymethyl ether, 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl propyloxymethyl ether, 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl butyloxymethyl ether, 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl pentyloxymethyl ether, 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl hexyloxymethyl ether, 16-hydroxy 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl alkoxymethyl ether compounds (n=6) such as 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl heptyloxymethyl ether, 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl octyloxymethyl ether, 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl nonyloxymethyl ether, 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl decyloxymethyl ether and 16-hydroxy-4,6,8,10,12,14-hexamethylheptadecyl benzyloxymethyl ether; 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl methoxymethyl ether, 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl ethoxymethyl ether, 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl propyloxymethyl ether, 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl butyloxymethyl ether, 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl pentyloxymethyl ether, 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl hexyloxymethyl ether, 18-hydroxy 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl alkoxymethyl ether compounds (n=7) such as 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl heptyloxymethyl ether, 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl octyloxymethyl ether, 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl nonyloxymethyl ether, 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl decyloxymethyl ether and 18-hydroxy-4,6,8,10,12,14,16-heptamethylnonadecyl benzyloxymethyl ether.

[0030] (b) Next, a method for producing a hydroxyalkyl alkoxymethyl ether compound (4) using the above (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) will be described below. Hydroxyalkyl alkoxymethyl ether compounds (4) can be prepared using the (2n+2)-alkoxymethoxyalkyl nucleophiles (2) described above.

[0031] [ka]

[0032] The production method includes at least a step of subjecting a (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) to a nucleophilic addition reaction with propylene oxide represented by the above general formula (3) to obtain a hydroxyalkyl alkoxymethyl ether compound (4).

[0033] In the above nucleophilic addition reaction, the (2n+2)-alkoxymethoxyalkyl nucleophile (2) may be one type or, if necessary, two or more types. The (2n+2)-alkoxymethoxyalkyl nucleophile (2) may also be independently synthesized as described in (i) above.

[0034] The propylene oxide (3) may be commercially available or may be independently synthesized.

[0035] In the nucleophilic addition reaction, the amount of the (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) used is preferably 0.6 to 1.3 moles per mole of propylene oxide (3) from the viewpoint of economic efficiency.

[0036] The nucleophilic addition reaction may be carried out in a solvent, if necessary. Examples of the solvent include common solvents, such as ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; N , N -dimethylformamide (DMF), N , N -Dimethylacetamide (DMAC), N -methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), gamma-butyrolactone (GBL), acetonitrile, N , NExamples of polar solvents include '-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, chloroform, and the like. From the viewpoint of reactivity, however, preferred are hydrocarbon solvents such as toluene and xylene; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran; and acetonitrile; and more preferred are tetrahydrofuran, 2-methyltetrahydrofuran, toluene, and xylene. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mole of the (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) from the viewpoint of reactivity.

[0037] The nucleophilic addition reaction may use a catalyst as necessary. Examples of the catalyst include monovalent copper halides such as cuprous chloride, cuprous bromide, and cuprous iodide; and divalent copper halides such as cupric chloride, cupric bromide, and cupric iodide. From the viewpoint of reactivity, the monovalent copper halides are preferred, and cuprous chloride is more preferred. The catalyst may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available catalysts may be used. The amount of the catalyst used is preferably 0.0001 to 0.300 mol, more preferably 0.0003 to 0.100 mol, per mol of the (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) from the viewpoint of reaction rate and / or post-treatment.

[0038] When the catalyst is used in the nucleophilic addition reaction, a cocatalyst may be used as necessary. Examples of the cocatalyst include phosphorus compounds such as trialkyl phosphite compounds having 3 to 9 carbon atoms, such as triethyl phosphite, and triarylphosphine compounds having 18 to 21 carbon atoms, such as triphenylphosphine, and the like. From the viewpoint of handling, trialkyl phosphite compounds having 3 to 9 carbon atoms, which are liquid at room temperature, are preferred. The co-catalyst may be one type or, if necessary, two or more types. In addition, the co-catalyst may be a commercially available product. When the cocatalyst is used, the amount of the cocatalyst used is preferably more than 0 to 0.500 mol, more preferably more than 0 to 0.200 mol, per 1 mol of the (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) from the viewpoint of reactivity. When a catalyst is used in the nucleophilic addition reaction, a lithium halide may be added, if necessary. The lithium halide includes lithium chloride, lithium bromide and lithium iodide, and from the viewpoint of reactivity, lithium chloride is preferred. When the lithium halide is used, the amount of the lithium halide used is preferably more than 0 and 0.250 mol per 1 mol of the (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) from the viewpoint of reactivity.

[0039] The reaction temperature in the nucleophilic addition reaction varies depending on the (2n+2)-alkoxymethoxyalkyl nucleophilic reagent (2) used, but from the viewpoint of reactivity, it is preferably −78 to 70° C., more preferably −20 to 50° C., and even more preferably 5 to 35° C. The reaction time in the nucleophilic addition reaction varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0040] (iii) Production method of haloalkyl alkoxymethyl ether compounds (1':n+1=2-8) (a) The haloalkyl alkoxymethyl ether compounds (1':n+1=2 to 8) are as described above. (b) Next, a method for producing a haloalkyl alkoxymethyl ether compound (1':n+1=2 to 8) will be described below. The haloalkyl alkoxymethyl ether compound (1': n+1 = 2 to 8) can be prepared using the above hydroxyalkyl alkoxymethyl ether compound (4).

[0041] [ka]

[0042] The production method includes a step of subjecting a hydroxyalkyl alkoxymethyl ether compound (4) to a halogenation reaction.

[0043] The halogenation reaction can be carried out, for example, by p This can be achieved by a method in which the hydroxyl group is tosylated using a -toluenesulfonyl halide compound and then halogenated using a lithium halide compound, which is a metal salt, or by a method in which the hydroxyl group is directly halogenated using a halogenating agent. Examples of the halogenating agent include halogens such as chlorine, bromine, and iodine; hydrogen halide compounds such as hydrogen chloride, hydrogen bromide, and hydrogen iodide; methanesulfonyl halide compounds such as methanesulfonyl chloride, methanesulfonyl bromide, and methanesulfonyl iodide; benzenesulfonyl halide compounds such as benzenesulfonyl chloride, benzenesulfonyl bromide, and benzenesulfonyl iodide; p -Toluenesulfonyl chloride, p -Toluenesulfonyl bromide and p -Toluenesulfonyl iodide etc. p -Toluenesulfonyl halide compounds; thionyl halide compounds such as thionyl chloride, thionyl bromide, and thionyl iodide; phosphorus halide compounds such as phosphorus trichloride, phosphorus pentachloride, and phosphorus tribromide; carbon tetrahalide compounds such as carbon tetrachloride, carbon tetrabromide, and carbon tetraiodide; trimethylsilyl chloride, trimethylsilyl bromide, trimethylsilyl iodide, triethylsilyl chloride, triethylsilyl bromide, triethylsilyl iodide, triisopropylsilyl chloride, triisopropylsilyl bromide, triisopropylsilyl iodide, third -Butyldimethylsilyl chloride, third -Butyldimethylsilyl bromide and third-butyldimethylsilyl iodide and other alkylsilyl halide compounds; oxalyl chloride, oxalyl bromide, oxalyl iodide and other oxalyl halide compounds; and N chlorosuccinimide, N -bromosuccinimide and N -Iodosuccinimide, etc. N From the viewpoint of suppressing side reactions, methanesulfonyl halide compounds, benzenesulfonyl halide compounds, and p -Toluenesulfonyl halide compounds and thionyl halide compounds are preferred, and methanesulfonyl halide compounds, benzenesulfonyl halide compounds and thionyl halide compounds are particularly preferred. The halogenating agent may be used alone or in combination of two or more as required. The halogenating agent may be a commercially available product. The amount of the halogenating agent used is preferably 0.8 to 5.0 mol, more preferably 1.0 to 2.5 mol, per mol of the hydroxyalkyl alkoxymethyl ether compound (4) from the viewpoint of reactivity.

[0044] In the halogenation reaction, a base may be used, if necessary. Examples of the base include hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide; carbonates such as sodium carbonate, potassium carbonate, calcium carbonate, and magnesium carbonate; and triethylamine, N , N -Diisopropylethylamine, piperidine, pyrrolidine, pyridine, lutidine, 4-dimethylaminopyridine, N , N -dimethylaniline, N , N -diethylaniline and amines such as 1,8-diazabicyclo[5.4.0]-7-undecene (DBU). As the halogenating agent, methanesulfonyl halide compounds, benzenesulfonyl halide compounds and pWhen a -toluenesulfonyl halide compound or the like is used, it is preferable to use an amine as the base, and it is more preferable to use a pyridine such as pyridine, lutidine, or 4-dimethylaminopyridine. When a thionyl halide compound is used as the halogenating agent, it is preferable to use an amine as the base, and it is more preferable to use a trialkylamine such as triethylamine. The base may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available bases may be used. When the base is used, the amount of the base used is preferably more than 0 to 8.0 mol, more preferably more than 0 to 3.0 mol, per mol of the hydroxyalkyl alkoxymethyl ether compound (4) from the viewpoint of yield and / or economic efficiency.

[0045] In the halogenation reaction, a metal salt may be added, if necessary. Examples of the metal salt include lithium salts such as lithium chloride, lithium bromide, and lithium iodide; sodium salts such as sodium chloride, sodium bromide, and sodium iodide; potassium salts such as potassium chloride, potassium bromide, and potassium iodide; calcium salts such as calcium chloride, calcium bromide, and calcium iodide; and magnesium salts such as magnesium chloride, magnesium bromide, and magnesium iodide. For example, when halogenation is carried out using a lithium halide compound, which is a metal salt, after tosylation, the reaction can be carried out using a lithium salt such as lithium chloride, lithium bromide, or lithium iodide. The metal salt may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available metal salts may be used. When the metal salt is used, the amount of the metal salt used is preferably more than 0 to 30.0 mol, more preferably more than 0 to 5.0 mol, per mol of the hydroxyalkyl alkoxymethyl ether compound (4) from the viewpoint of reactivity. By adding the metal salt, the halide concentration in the reaction system can be increased, thereby increasing the reactivity. However, when economic and / or environmental considerations are taken into account, it is preferable to carry out the reaction without using a metal salt.

[0046] The halogenation reaction may be carried out in the presence of a solvent, if necessary. Examples of the solvent include common solvents, such as ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; N , N -dimethylformamide (DMF), N , N -Dimethylacetamide (DMAC), N polar solvents such as N,N'-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), γ-butyrolactone (GBL), acetonitrile, acetone, N,N'-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform; and ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, and n-butyl acetate. From the viewpoint of reactivity, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, dichloromethane, chloroform, γ-butyrolactone, N -Methylpyrrolidone, N , N -dimethylformamide, N , N -Dimethylacetamide and acetonitrile are preferred, and from the viewpoint of safety, 2-methyltetrahydrofuran, γ-butyrolactone and acetonitrile are particularly preferred. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. When a solvent is used in the halogenation reaction, the amount of the solvent used is preferably more than 0 to 3000 g, more preferably more than 0 to 800 g, per mol of the hydroxyalkyl alkoxymethyl ether compound (4). Since the use of such a solvent reduces the amount of the reaction mixture and decreases the productivity, the reaction may be carried out using a base as a solvent without using the above-mentioned solvent.

[0047] The reaction temperature in the halogenation reaction varies depending on the halogenating agent used, but is preferably 5 to 180°C, more preferably 20 to 120°C, from the viewpoint of reactivity. The reaction time in the halogenation reaction varies depending on the halogenating agent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0048] In this manner, a haloalkyl alkoxymethyl ether compound (1':n+1) with 3 carbons can be produced from the haloalkyl alkoxymethyl ether compound (1:n).Then, the produced haloalkyl alkoxymethyl ether compound (1') is used as the haloalkyl alkoxymethyl ether compound (1:n) to convert it into a nucleophilic reagent, and then the nucleophilic addition reaction of the nucleophilic reagent to propylene oxide and the halogenation reaction are repeated, so that n of the haloalkyl alkoxymethyl ether compound (1) can be freely increased. In other words, the number of methyl branches can be increased as much as desired, and as shown in the reaction scheme below, this method can be used to comprehensively produce a variety of compounds with a 1,3-dimethyl skeleton, such as 2,4,6,8-tetramethyl-1-undecanol, 2,4,6,8,10,12,14,16-octamethylheptadecane, 4,6,8,10,16-pentamethyldocosane, and 4,6,8,10,16,18-hexamethyldocosane.

[0049] [ka]

[0050] III. Method for preparing haloalkyl alkoxymethyl ether compounds (1:n=1) A haloalkyl alkoxymethyl ether compound (1:n=1) (which may also be called a 4-halopentyl alkoxymethyl ether compound) represented by the above general formula (1) where n is 1, is produced, for example, according to the production method shown in the following chemical reaction scheme.

[0051] [ka]

[0052] That is, the above-mentioned haloalkyl alkoxymethyl ether compound (1:n=1) (4-haloalkyl alkoxymethyl ether compound) can be produced by ring-opening 2-methyltetrahydrofuran with an acid halide, followed by deprotection of the acyl group and alkoxymethylation of the hydroxyl group.

[0053] (i) 4-halopentyl acylate compound (13) and its production method (a) The 4-halopentyl acylate compound (13) is explained below. The 4-halopentyl acylate compound (13) is represented by the following general formula (13).

[0054] [ka] In the above general formula (13), R 2 represents an alkyl group having 1 to 9 carbon atoms or a phenyl group; X 1 is as defined in general formulas (1) and (1'). The alkyl group R 2 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and third -butyl group. Halogen atom X 1Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of reactivity, a chlorine atom and a bromine atom are preferred, and a chlorine atom is particularly preferred.

[0055] Specific examples of the 4-halopentyl acylate compound (13) include 4-chloropentyl acetate, 4-bromopentyl acetate, 4-iodopentyl acetate, 4-chloropentyl propionate, 4-bromopentyl propionate, 4-iodopentyl propionate, 4-chloropentyl butyrate, 4-bromopentyl butyrate, 4-iodopentyl butyrate, 4-chloropentyl valerate, 4-bromopentyl valerate, 4-iodopentyl valerate, 4-chloropentyl pivaloate, 4-bromopentyl pivaloate, 4-iodopentyl pivaloate, 4-chloropentyl benzoate, 4-bromopentyl benzoate, and 4-iodopentyl benzoate.

[0056] (b) Next, a method for producing the above 4-halopentyl acylate compound (13) will be described below. The 4-halopentyl acylate compound (13) can be prepared using 2-methyltetrahydrofuran and an acid halide (12) as shown in the following reaction scheme. [ka]

[0057] The preparation method includes a step of ring-opening 2-methyltetrahydrofuran with an acid halide (12).

[0058] The acid halide (12) is described below. The acid halide (12) is represented by the following general formula (12). [ka] In the general formula (12), R 2 and X 1is as defined in general formula (13).

[0059] Specific examples of the acid halide (12) include acetyl halide compounds such as acetyl chloride, acetyl bromide, and acetyl iodide; propionyl halide compounds such as propionyl chloride, propionyl bromide, and propionyl iodide; butyryl halide compounds such as butyryl chloride, butyryl bromide, and butyryl iodide; valeryl halide compounds such as valeryl chloride, valeryl bromide, and valeryl iodide; pivaloyl halide compounds such as pivaloyl chloride, pivaloyl bromide, and pivaloyl iodide; and benzoyl halide compounds such as benzoyl chloride, benzoyl bromide, and benzoyl iodide.

[0060] The amount of the acid halide (12) used is preferably 0.7 to 1.5 mol, more preferably 0.8 to 1.1 mol, per mol of 2-methyltetrahydrofuran, from the viewpoint of completing the reaction.

[0061] In the ring-opening reaction, a catalyst may be used as necessary. Examples of the catalyst include zinc halide compounds such as zinc chloride, zinc bromide, and zinc iodide; titanium compounds such as titanium tetrachloride, titanium tetrabromide, titanium(IV) methoxide, titanium(IV)=ethoxide, titanium(IV)=isopropoxide, and titanium(IV) oxide; and zirconium compounds such as zirconium oxide. From the viewpoint of reactivity, zinc halide compounds are preferred. The catalyst may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available catalysts may be used. The amount of the catalyst used is preferably 0.0001 to 0.3 mol, and more preferably 0.001 to 0.1 mol, per 1 mol of 2-methyltetrahydrofuran, from the viewpoint of completing the reaction.

[0062] The ring-opening reaction may be carried out in the presence of a solvent, if necessary. The solvent may be any solvent that does not affect the reaction, such as a hydrocarbon solvent such as hexane, heptane, benzene, toluene, xylene, or cumene. From the viewpoint of productivity, 2-methyltetrahydrofuran is used as both a solvent and a substrate, and in this case, no other solvent may be used. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. When the solvent is used, the amount of the solvent used is preferably more than 0 to 3000 g, and more preferably more than 0 to 500 g, per 1 mol of 2-methyltetrahydrofuran, from the viewpoint of reactivity.

[0063] The reaction temperature varies depending on the reaction scale, but is preferably from -15 to 85°C, more preferably from -10 to 45°C, from the viewpoint of reactivity. The reaction time varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0064] (ii) 4-halo-1-pentanol compound (15) and its production method (a) The 4-halo-1-pentanol compound (15) is described below. The 4-halo-1-pentanol compound (15) is represented by the following general formula (15). [ka] In the above general formula (15), X 1 is as defined in general formula (12).

[0065] Specific examples of the 4-halo-1-pentanol compound (15) include 4-chloro-1-pentanol, 4-bromo-1-pentanol, and 4-iodo-1-pentanol.

[0066] (b) A method for producing the above 4-halo-1-pentanol compound (15) is described below. The 4-halo-1-pentanol compound (15) can be prepared by converting the acyl group of the 4-halopentyl acylate compound (13) into an organometallic reagent R 3 M 3 It can be prepared by deacylation with (14).

[0067] [ka]

[0068] In the above general formula (14), R 3 represents an alkyl group or an ethynyl group having 1 to 14 carbon atoms, preferably 1 to 8 carbon atoms. The alkyl group R 3 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, and a tetradecyl group. In the above general formula (14), M 3 Li, Na, K, Ag, MgZ 1 , or CaZ 1 where Z 1 is a halogen atom or R 3 Represents the halogen atom Z 1 Examples of the aryl group include a chlorine atom, a bromine atom, and an iodine atom.

[0069] Organometallic Reagents R 3 M 3Specific examples of (14) include alkyl lithiums such as methyl lithium, ethyl lithium, propyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, pentyl lithium, hexyl lithium, heptyl lithium, octyl lithium, nonyl lithium, and decyl lithium; methyl magnesium halide compounds such as methyl magnesium chloride, methyl magnesium bromide, and methyl magnesium iodide; ethyl magnesium halide compounds such as ethyl magnesium chloride, ethyl magnesium bromide, and ethyl magnesium iodide; propyl magnesium halide compounds such as propyl magnesium chloride, propyl magnesium bromide, and propyl magnesium iodide; butyl magnesium halide compounds such as butyl magnesium chloride, butyl magnesium bromide, and butyl magnesium iodide; pentyl magnesium compounds such as pentyl magnesium chloride, pentyl magnesium bromide, and pentyl magnesium iodide. heptylmagnesium halide compounds such as heptylmagnesium chloride, heptylmagnesium bromide and heptylmagnesium iodide; octylmagnesium halide compounds such as octylmagnesium chloride, octylmagnesium bromide and octylmagnesium iodide; nonylmagnesium halide compounds such as nonylmagnesium chloride, nonylmagnesium bromide and nonylmagnesium iodide; Grignard reagents such as decylmagnesium halide compounds such as decylmagnesium chloride, decylmagnesium bromide and decylmagnesium iodide; and metal acetylides such as lithium acetylide, sodium acetylide, potassium acetylide, calcium acetylide and silver acetylide. From the viewpoint of reactivity, Grignard reagents are preferred.

[0070] Organometallic Reagents R 3 M 3The amount of (14) used is preferably 1.5 to 5.0 mol, more preferably 2.0 to 3.5 mol, per mol of the 4-halopentyl acylate compound (13) from the viewpoint of completing the reaction.

[0071] A solvent may be used for the deacylation, if necessary. Examples of the solvent include common solvents, such as ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; and N , N -dimethylformamide (DMF), N , N -Dimethylacetamide (DMAC), N -methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), gamma-butyrolactone (GBL), acetonitrile, N , N Examples of polar solvents include '-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, chloroform, and the like. From the viewpoint of reactivity, however, preferred are hydrocarbon solvents such as toluene and xylene; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran; and acetonitrile; and more preferred are tetrahydrofuran, 2-methyltetrahydrofuran, toluene, and xylene. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. When a solvent is used in the deacylation, the amount of the solvent used is preferably more than 0 to 5000 g, more preferably more than 0 to 3000 g, per 1 mol of the 4-halopentyl acylate compound (13) from the viewpoint of reactivity.

[0072] The reaction temperature in the deacylation varies depending on the reaction scale, but is preferably −15 to 90° C., more preferably 10 to 50° C., from the viewpoint of reactivity. The reaction time for the deacylation varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0073] (iii) 4-halopentyl alkoxymethyl ether compound (1:n=1) and its production method (a) The 4-halopentyl alkoxymethyl ether compound (1:n=1) is as described above. (b) Next, a method for producing a 4-halopentyl alkoxymethyl ether compound (1:n=1) will be described below. The 4-halopentyl alkoxymethyl ether compound (1:n=1) can be prepared using the above 4-halo-1-pentanol compound (15).

[0074] [ka]

[0075] The process comprises the step of alkoxymethylating a 4-halo-1-pentanol compound (15) with a halomethyl alkyl ether compound (16).

[0076] The halomethyl alkyl ether compound (16) is described below. The halomethyl alkyl ether compound (16) is represented by the following general formula (16).

[0077] [ka]

[0078] In the above general formula (16), X 5 represents a halogen atom. Halogen atom X 5Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of reactivity, a chlorine atom and a bromine atom are preferred, and a chlorine atom is particularly preferred. In the above general formula (16), R 1 is as defined in the above general formulas (1) and (1').

[0079] Specific examples of the halomethyl alkyl ether compound (16) include the following compounds: chloromethyl alkyl ether compounds such as chloromethyl methyl ether, chloromethyl ethyl ether, chloromethyl propyl ether, chloromethyl butyl ether, chloromethyl pentyl ether, chloromethyl hexyl ether, chloromethyl heptyl ether, chloromethyl octyl ether, chloromethyl nonyl ether and chloromethyl decyl ether; Chloromethyl benzyl ether; bromomethyl alkyl ether compounds such as bromomethyl methyl ether, bromomethyl ethyl ether, bromomethyl propyl ether, bromomethyl butyl ether, bromomethyl pentyl ether, bromomethyl hexyl ether, bromomethyl heptyl ether, bromomethyl octyl ether, bromomethyl nonyl ether and bromomethyl decyl ether; Bromomethyl benzyl ether; iodomethyl alkyl ether compounds, such as iodomethyl methyl ether, iodomethyl ethyl ether, iodomethyl propyl ether, iodomethyl butyl ether, iodomethyl pentyl ether, iodomethyl hexyl ether, iodomethyl heptyl ether, iodomethyl octyl ether, iodomethyl nonyl ether and iodomethyl decyl ether; and Iodomethyl benzyl ether, etc. From the viewpoint of versatility, chloromethyl methyl ether, chloromethyl ethyl ether, chloromethyl propyl ether, chloromethyl butyl ether and chloromethyl benzyl ether are preferred, and chloromethyl methyl ether and chloromethyl ethyl ether are more preferred.

[0080] The halomethyl alkyl ether compounds (16) can be commercially available or independently synthesized (see, for example, Example 5 below).

[0081] The amount of the halomethyl alkyl ether compound (16) used is preferably 1.0 to 3.0 mol, more preferably 1.0 to 1.8 mol, per mol of the 4-halo-1-pentanol compound (15) from the viewpoint of completing the reaction.

[0082] In the alkoxymethylation reaction, a base may be used, if necessary. The base may be triethylamine, N , N -Diisopropylethylamine, piperidine, pyrrolidine, pyridine, lutidine, 4-dimethylaminopyridine, N , N -dimethylaniline, N , N -diethylaniline, N , N -dipropylaniline, N , N -dibutylaniline and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU). The base may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available bases may be used. The amount of the base used is preferably 0.1 to 4.0 mol, more preferably 1.0 to 2.5 mol, per mol of the 4-halo-1-pentanol compound (15), from the viewpoints of yield and economic efficiency.

[0083] The alkoxymethylation may be carried out in the presence of a solvent, if necessary. Examples of the solvent include common solvents, such as ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; N , N -dimethylformamide (DMF), N , N -Dimethylacetamide (DMAC), N -methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), gamma-butyrolactone (GBL), acetonitrile, N , N Examples of the solvent include polar solvents such as '-dimethylpropylene urea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform; and ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, and n-butyl acetate. From the viewpoint of reactivity, however, hydrocarbon solvents such as toluene and xylene, and ester solvents such as methyl acetate and ethyl acetate are preferred. In order to avoid a decrease in productivity, the alkoxymethylation may be carried out without a solvent. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. When a solvent is used in the alkoxymethylation, the amount of the solvent used is preferably more than 0 and 1500 g per 1 mol of the 4-halo-1-pentanol compound (15).

[0084] The reaction temperature in the alkoxymethylation varies depending on the reaction scale, but is preferably from -15 to 60°C, more preferably from 10 to 40°C, from the viewpoint of reactivity. The reaction time for the alkoxymethylation varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0085] IV. Method for producing 4,6,8,10,16-pentamethyldocosane (11) One of the target compounds of the present invention, 4,6,8,10,16-pentamethyldocosane represented by the following general formula (11), is produced from the above-mentioned 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophilic reagent (2:n=3) according to the production method shown in the following chemical reaction formula.

[0086] [ka]

[0087] That is, 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophilic reagent (2:n=3) is subjected to a coupling reaction with 1-halo-2-methylpentane compound (5) to produce 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6), which is then subjected to a dealkoxymethylation reaction to produce 4,6,8,10-tetramethyltridecanol (7). Next, 4,6,8,10-tetramethyltridecanol (7) is subjected to a halogenation reaction to produce 1-halo-4,6,8,10-tetramethyltridecane compound (8). The 1-halo-4,6,8,10-tetramethyltridecane compound (8) can then be converted to a 4,6,8,10-tetramethyltridecyl nucleophile (9), which can then be subjected to a coupling reaction with a 1-halo-3-methylnonane compound (10).

[0088] (i) Method for producing 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) (a) The above 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) is explained below. The 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) is represented by the following general formula (6). [ka] In the above general formula (6), R 1 R is as defined in the above general formulas (1) and (1'). 1 When is an n-alkyl group, it preferably has 1 to 9 carbon atoms, and more preferably has 1 to 4 carbon atoms.

[0089] Specific examples of the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) include 4,6,8,10-tetramethyltridecyl methoxymethyl ether, 4,6,8,10-tetramethyltridecyl ethoxymethyl ether, 4,6,8,10-tetramethyltridecyl propyloxymethyl ether, 4,6,8,10-tetramethyltridecyl butyloxymethyl ether, 4,6,8,10-tetramethyltridecyl pentyloxymethyl ether, Examples of the methyltridecyl ether include 4,6,8,10-tetramethyltridecyl hexyloxymethyl ether, 4,6,8,10-tetramethyltridecyl heptyloxymethyl ether, 4,6,8,10-tetramethyltridecyl octyloxymethyl ether, 4,6,8,10-tetramethyltridecyl nonyloxymethyl ether, 4,6,8,10-tetramethyltridecyl decyloxymethyl ether, and 4,6,8,10-tetramethyltridecyl benzyloxymethyl ether.

[0090] (b) Next, a method for producing the above 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) will be described below. For example, the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) can be prepared using an 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophilic reagent represented by the following general formula (2: n=3) and a 1-halo-2-methylpentane compound represented by the following general formula (5), as shown in the following chemical reaction formula.

[0091] [ka]

[0092] The preparation method includes a step of subjecting an 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile (2:n=3) to a coupling reaction with a 1-halo-2-methylpentane compound (5).

[0093] The above 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile (2:n=3) is explained below. 8-Alkoxymethoxy-1,3,5-trimethyloctyl nucleophilic reagent (2:n=3) is represented by the following general formula (2:n=3). [ka] In the above general formula (2: n = 3), M 1 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 where Z 1 represents a halogen atom or an 8-alkoxymethoxy-1,3,5-trimethyloctyl group. 1 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of reactivity, a chlorine atom and a bromine atom are preferred, and a chlorine atom is particularly preferred. In the above general formula (2: n = 3), M 1 MgZ 1 When the 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile (2:n=3,M 1B =MgZ 1B ) is a Grignard reagent.

[0094] Specific examples of 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophiles (2:n=3) include the following; 8-alkoxymethoxy-1,3,5-trimethyloctyllithium reagents such as 8-methoxymethoxy-1,3,5-trimethyloctyllithium, 8-ethoxymethoxy-1,3,5-trimethyloctyllithium, 8-propyloxymethoxy-1,3,5-trimethyloctyllithium and 8-butyloxymethoxy-1,3,5-trimethyloctyllithium; 8-Methoxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-ethoxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-propyloxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-butyloxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-pentyloxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-hexyloxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-heptyloxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-Octyloxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-Nonyloxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-Benzyloxymethoxy-1,3,5-trimethyloctylmagnesium chloride, 8-Methoxymethoxy-1,3,5-trimethyloctylmagnesium bromide, 8-Ethoxymethoxy-1,3,5-trimethyloctylmagnesium bromide, 8-Propyloxymethoxy 8-Butyloxymethoxy-1,3,5-trimethyloctylmagnesium bromide, 8-Pentyloxymethoxy-1,3,5-trimethyloctylmagnesium bromide, 8-Hexyloxymethoxy-1,3,5-trimethyloctylmagnesium bromide, 8-Heptyloxymethoxy-1,3,5-trimethyloctylmagnesium bromide, 8-Octyloxymethoxy-1,3,5-trimethyloctylmagnesium bromide, 8-Nonyloxymethoxy 1,3,5-trimethyloctylmagnesium bromide, 8-benzyloxymethoxy-1,3,5-trimethyloctylmagnesium bromide, 8-methoxymethoxy-1,3,5-trimethyloctylmagnesium iodide, 8-ethoxymethoxy-1,3,5-trimethyloctylmagnesium iodide, 8-propyloxymethoxy-1,3,5-trimethyloctylmagnesium iodide, 8-butyloxymethoxy-1,3,5-trimethyloctylmagnesium iodide, 8-pentyloxymethoxy-1,3,8-Alkoxymethoxy-1,3,5-trimethyloctylmagnesium halide reagents (M, such as 5-trimethyloctylmagnesium iodide, 8-hexyloxymethoxy-1,3,5-trimethyloctylmagnesium iodide, 8-heptyloxymethoxy-1,3,5-trimethyloctylmagnesium iodide, 8-octyloxymethoxy-1,3,5-trimethyloctylmagnesium iodide, 8-nonyloxymethoxy-1,3,5-trimethyloctylmagnesium iodide, and 8-benzyloxymethoxy-1,3,5-trimethyloctylmagnesium iodide) 1 =MgZ 1 (The above is a Grignard reagent); Bis[8-alkoxymethoxy-1,3,5-trimethyloctyl]cuprate (M) such as bis[8-methoxymethoxy-1,3,5-trimethyloctyl]cuprate, bis[8-ethoxymethoxy-1,3,5-trimethyloctyl]cuprate, bis[8-propyloxymethoxy-1,3,5-trimethyloctyl]cuprate and bis[8-butyloxymethoxy-1,3,5-trimethyloctyl]cuprate 1 =CuZ 1 ); and Gilman reagents such as lithium bis[8-alkoxymethoxy-1,3,5-trimethyloctyl]cuprate, lithium bis[8-methoxymethoxy-1,3,5-trimethyloctyl]cuprate, lithium bis[8-ethoxymethoxy-1,3,5-trimethyloctyl]cuprate, lithium bis[8-propyloxymethoxy-1,3,5-trimethyloctyl]cuprate, and lithium bis[8-butyloxymethoxy-1,3,5-trimethyloctyl]cuprate (M 1 =CuLiZ 1 (The above is a Gilman reagent.) From the viewpoint of reactivity, a Grignard reagent such as 8-alkoxymethoxy-1,3,5-trimethyloctylmagnesium halide reagent is preferred.

[0095] The above 1-halo-2-methylpentane compound (5) will be explained below. The 1-halo-2-methylpentane compound (5) is represented by the following general formula (5). [ka] In the above general formula (5), X 2 represents a halogen atom. Halogen atom X 2 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of reactivity, a bromine atom and an iodine atom are preferred, and a bromine atom is particularly preferred.

[0096] Specific examples of the 1-halo-2-methylpentane compound (5) include 1-chloro-2-methylpentane, 1-bromo-2-methylpentane, and 1-iodo-2-methylpentane, and from the viewpoint of yield, 1-bromo-2-methylpentane and 1-iodo-2-methylpentane are preferred. The 1-halo-2-methylpentane compound (5) may be used alone or in combination with two or more compounds as required. The 1-halo-2-methylpentane compound (5) may be a commercially available compound or may be independently synthesized.

[0097] The 1-halo-2-methylpentane compound (5) can be prepared, for example, by halogenating 2-methylpentanol.

[0098] Next, the coupling reaction of 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophilic reagent (2:n=3) with 1-halo-2-methylpentane compound (5) will be described below. In the coupling reaction, the amount of the 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophilic reagent (2:n=3) used is preferably 0.8 to 1.4 moles per mole of the 1-halo-2-methylpentane compound (5) from the viewpoint of economic efficiency.

[0099] The coupling reaction may be carried out in the presence of a solvent, if necessary. Examples of the solvent include common solvents, such as ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; N , N -dimethylformamide (DMF), N , N -Dimethylacetamide (DMAC), N -methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), gamma-butyrolactone (GBL), acetonitrile, N , N Examples of polar solvents include '-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, chloroform, and the like. From the viewpoint of reactivity, however, preferred are hydrocarbon solvents such as toluene and xylene; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran; and acetonitrile; and more preferred are tetrahydrofuran, 2-methyltetrahydrofuran, toluene, and xylene. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mole of the 1-halo-2-methylpentane compound (5) from the viewpoint of reactivity.

[0100] The coupling reaction may use a catalyst as necessary. Examples of the catalyst include monovalent copper halides such as copper(I) chloride, copper(I) bromide, and copper(I) iodide; and divalent copper halides such as copper(II) chloride, copper(II) bromide, and copper(II) iodide. From the viewpoint of reactivity, the monovalent copper halides are preferred, and copper(I) iodide is more preferred. The catalyst may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available catalysts may be used. The amount of the catalyst used is preferably 0.0003 to 0.3 mol, more preferably 0.001 to 0.1 mol, per mol of the 1-halo-2-methylpentane compound (5), from the viewpoint of reaction rate and / or post-treatment.

[0101] When a catalyst is used in the coupling reaction, a cocatalyst may be used as necessary. Examples of the cocatalyst include phosphorus compounds such as trialkyl phosphite compounds having 3 to 9 carbon atoms, such as triethyl phosphite, and triarylphosphine compounds having 18 to 21 carbon atoms, such as triphenylphosphine, among which trialkyl phosphite compounds are preferred from the viewpoint of reactivity. The co-catalyst may be one type or, if necessary, two or more types. In addition, the co-catalyst may be a commercially available product. The amount of the cocatalyst used is preferably 0.001 to 0.500 mol, more preferably 0.005 to 0.200 mol, per 1 mol of the 1-halo-2-methylpentane compound (5) from the viewpoint of reactivity.

[0102] When a catalyst is used in the coupling reaction, a lithium halide may be added as necessary. Examples of the lithium halide include lithium chloride, lithium bromide, and lithium iodide, and from the viewpoint of reactivity, lithium chloride is preferred. The amount of lithium halide used in the coupling reaction is preferably 0.005 to 0.250 mol per 1 mol of the 1-halo-2-methylpentane compound (5) from the viewpoint of reactivity.

[0103] The reaction temperature in the coupling reaction varies depending on the 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophilic reagent (2:n=3) used, but from the viewpoint of reactivity, it is preferably −78 to 70° C., more preferably −20 to 50° C., and even more preferably 5 to 35° C. The reaction time in the coupling reaction varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0104] (ii) Method for producing 4,6,8,10-tetramethyltridecanol (7) A method for producing 4,6,8,10-tetramethyltridecanol (7) will be described below. 4,6,8,10-Tetramethyltridecanol (7) can be prepared, for example, by using the above-mentioned 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) as shown in the following chemical reaction formula.

[0105] [ka]

[0106] The production method includes a step of subjecting a 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) to a dealkoxymethylation reaction.

[0107] The dealkoxymethylation reaction is carried out by reacting R 1 The optimum conditions vary depending on the type. For example, R 1 When R is a phenyl group, dealkoxymethylation can be achieved by Birch reduction using sodium in liquid ammonia, while R 1 However, when the alkoxy group is a hydrogen atom or an n-alkyl group such as a methyl group, an ethyl group, a propyl group, or a butyl group, dealkoxymethylation can be carried out using an acid and water or an alcohol compound (17).

[0108] For example, the acid may be inorganic acids such as hydrochloric acid and hydrobromic acid; p - Sulfonic acids such as toluenesulfonic acid and benzenesulfonic acid; organic acids such as trifluoroacetic acid, acetic acid, formic acid and oxalic acid; Lewis acids such as iodotrimethylsilane and titanium tetrachloride. From the viewpoint of suppressing side reactions, p toluenesulfonic acid, benzenesulfonic acid, hydrochloric acid and hydrobromic acid are preferred, p Toluenesulfonic acid, hydrochloric acid and hydrobromic acid are particularly preferred. The acid may be used alone or in combination with two or more acids as required. In addition, commercially available acids may be used. The amount of the acid used is preferably 0.0001 to 10.0 mol, more preferably 0.001 to 1.0 mol, per 1 mol of the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6).

[0109] The alcohol compound (17) is represented by the following general formula (17). R 4 OH (17) R 4 represents a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 6 carbon atoms, and from the viewpoint of cost or versatility, a monovalent hydrocarbon group having 1 to 6 carbon atoms is preferred. The monovalent hydrocarbon group is a linear saturated hydrocarbon group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, or an n-dodecyl group; an isopropyl group, second Examples of the hydrocarbon groups include branched saturated hydrocarbon groups such as 2-butyl and 2-methylbutyl groups, linear unsaturated hydrocarbon groups such as 2-propenyl groups, branched unsaturated hydrocarbon groups such as 2-methyl-2-propenyl groups, and cyclic saturated hydrocarbon groups such as cyclopropyl groups, and are also usable as isomeric hydrocarbon groups. In addition, some of the hydrogen atoms of these hydrocarbon groups may be substituted with methyl groups, ethyl groups, hydroxyl groups, or the like. As the monovalent hydrocarbon group, from the viewpoint of ease of handling of the alcohol compound (17) (including, for example, cost and ease of removal due to a low boiling point) and / or the amount of the alcohol compound used, a methyl group, an ethyl group, an n-propyl group, and an n-butyl group are preferred.

[0110] Examples of the alcohol compound (17) include linear alcohols such as methanol, ethanol, n-propanol, n-butanol, n-pentanol, n-hexanol, n-heptanol, n-octanol, n-nonanol, n-decanol, n-undecanol, n-dodecanol, n-tridecanol, n-tetradecanol, and n-pentadecanol; branched alcohols such as isopropanol and 2-butanol; and diols such as ethylene glycol, propylene glycol, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 1,2-dimethyl-1,3-propanediol, 1,3-dimethyl-1,3-propanediol, and 2-methyl-1,4-butanediol. From the viewpoint of reactivity, methanol and ethanol are preferred, and methanol is particularly preferred. The alcohol compound (17) may be used alone or in combination with two or more kinds, if necessary. The alcohol compound (17) may be a commercially available product. The amount of the alcohol compound (17) used is preferably 1 to 1000 mol, more preferably 1 to 100 mol, per 1 mol of the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) from the viewpoint of reactivity.

[0111] When water is used, the amount of water used is preferably more than 0 to 1000 mol, more preferably more than 0 to 100 mol, per 1 mol of the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) from the viewpoint of reactivity.

[0112] In the dealkoxymethylation reaction, a solvent other than the alcohol compound (17) may be used, if necessary. Examples of the solvent include common solvents, such as ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene;N , N -dimethylformamide (DMF), N , N -Dimethylacetamide (DMAC), N -methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), gamma-butyrolactone (GBL), acetonitrile, N , N Examples of suitable solvents include polar solvents such as '-dimethylpropylene urea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform; ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, and n-butyl acetate; and water. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. When a solvent is used in the dealkoxymethylation reaction, the amount of the solvent used is preferably more than 0 to 2000 g, more preferably more than 0 to 500 g, per mol of the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6). The use of the solvent reduces the amount of the reaction mixture and decreases the productivity, so the dealkoxymethylation may be carried out without using any of the above solvents.

[0113] The reaction temperature in the dealkoxymethylation reaction varies depending on the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) used, but is preferably −5 to 180° C., more preferably 10 to 130° C., from the viewpoint of reactivity. The reaction time in the dealkoxymethylation reaction varies depending on the 4,6,8,10-tetramethyltridecyl alkoxymethyl ether compound (6) used or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0114] In the dealkoxymethylation reaction, the by-product alkoxymethoxymethane may be removed by distillation from the reaction system, if necessary. By removing the alkoxymethoxymethane from the reaction system, the equilibrium shifts to the product side, making it possible to shorten the reaction time.

[0115] (iii) 1-Halo-4,6,8,10-tetramethyltridecane compound (8) and its production method (a) The above 1-halo-4,6,8,10-tetramethyltridecane compound (8) is explained below. The 1-halo-4,6,8,10-tetramethyltridecane compound (8) is represented by the following general formula (8). [ka] (In the formula, X 3 represents a halogen atom.) In the above general formula (8), X 3 represents a halogen atom. Halogen atom X 3 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of reactivity, a chlorine atom and a bromine atom are preferred, and a chlorine atom is particularly preferred. (b) Next, a method for producing the above 1-halo-4,6,8,10-tetramethyltridecane compound (8) will be described. The 1-halo-4,6,8,10-tetramethyltridecane compound (8) can be prepared, for example, using 4,6,8,10-tetramethyltridecanol represented by the following general formula (7), as shown in the following chemical reaction formula.

[0116] [ka]

[0117] The production method includes a step of subjecting 4,6,8,10-tetramethyltridecanol (7) to a halogenation reaction.

[0118] The halogenation reaction can be carried out, for example, by pThis can be achieved by a method in which the hydroxyl group is tosylated using a -toluenesulfonyl halide compound and then halogenated using a lithium halide compound, which is a metal salt, or by a method in which the hydroxyl group is directly halogenated using a halogenating agent.

[0119] Examples of the halogenating agent include halogens such as chlorine, bromine, and iodine; hydrogen halide compounds such as hydrogen chloride, hydrogen bromide, and hydrogen iodide; methanesulfonyl halide compounds such as methanesulfonyl chloride, methanesulfonyl bromide, and methanesulfonyl iodide; benzenesulfonyl halide compounds such as benzenesulfonyl chloride, benzenesulfonyl bromide, and benzenesulfonyl iodide; p -Toluenesulfonyl chloride, p -Toluenesulfonyl bromide and p -Toluenesulfonyl iodide etc. p -Toluenesulfonyl halide compounds; thionyl halide compounds such as thionyl chloride, thionyl bromide, and thionyl iodide; phosphorus halide compounds such as phosphorus trichloride, phosphorus pentachloride, and phosphorus tribromide; carbon tetrahalide compounds such as carbon tetrachloride, carbon tetrabromide, and carbon tetraiodide; trimethylsilyl chloride, trimethylsilyl bromide, trimethylsilyl iodide, triethylsilyl chloride, triethylsilyl bromide, triethylsilyl iodide, triisopropylsilyl chloride, triisopropylsilyl bromide, triisopropylsilyl iodide, third -Butyldimethylsilyl chloride, third -Butyldimethylsilyl bromide and third -butyldimethylsilyl iodide and other alkylsilyl halide compounds; oxalyl chloride, oxalyl bromide, oxalyl iodide and other oxalyl halide compounds; and N chlorosuccinimide, N -bromosuccinimide and N -Iodosuccinimide, etc. NFrom the viewpoint of suppressing side reactions, methanesulfonyl halide compounds, benzenesulfonyl halide compounds, and p -Toluenesulfonyl halide compounds and thionyl halide compounds are preferred, and methanesulfonyl halide compounds, benzenesulfonyl halide compounds and thionyl halide compounds are particularly preferred. The halogenating agent may be used alone or in combination of two or more as required. The halogenating agent may be a commercially available product. The amount of the halogenating agent used is preferably 0.8 to 5.0 mol, and more preferably 1.0 to 2.5 mol, per mol of 4,6,8,10-tetramethyltridecanol (7) from the viewpoint of reactivity.

[0120] In the halogenation reaction, a base may be used, if necessary. Examples of the base include hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide; carbonates such as sodium carbonate, potassium carbonate, calcium carbonate, and magnesium carbonate; and triethylamine, N , N -Diisopropylethylamine, piperidine, pyrrolidine, pyridine, lutidine, 4-dimethylaminopyridine, N , N -dimethylaniline, N , N -diethylaniline and amines such as 1,8-diazabicyclo[5.4.0]-7-undecene (DBU). As the halogenating agent, methanesulfonyl halide compounds, benzenesulfonyl halide compounds and p When a -toluenesulfonyl halide compound or the like is used, it is preferable to use an amine as the base, and it is more preferable to use a pyridine such as pyridine, lutidine, or 4-dimethylaminopyridine. When a thionyl halide compound is used as the halogenating agent, it is preferable to use an amine as the base, and it is more preferable to use a trialkylamine such as triethylamine. The base may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available bases may be used. When the base is used, the amount of the base used is preferably more than 0 to 8.0 mol, more preferably more than 0 to 3.0 mol, per mol of 4,6,8,10-tetramethyltridecanol (7) from the viewpoint of yield and / or economic efficiency.

[0121] In the halogenation reaction, a metal salt may be added, if necessary. Examples of the metal salt include lithium salts such as lithium chloride, lithium bromide, and lithium iodide; sodium salts such as sodium chloride, sodium bromide, and sodium iodide; potassium salts such as potassium chloride, potassium bromide, and potassium iodide; calcium salts such as calcium chloride, calcium bromide, and calcium iodide; and magnesium salts such as magnesium chloride, magnesium bromide, and magnesium iodide. For example, when halogenation is carried out using a lithium halide compound, which is a metal salt, after tosylation, the reaction can be carried out using a lithium salt such as lithium chloride, lithium bromide, or lithium iodide. The metal salt may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available metal salts may be used. When the metal salt is used, the amount of the metal salt used is preferably more than 0 to 30.0 mol, and more preferably more than 0 to 5.0 mol, per mol of 4,6,8,10-tetramethyltridecanol (7) from the viewpoint of reactivity. By adding the metal salt, the halide concentration in the reaction system can be increased, thereby increasing the reactivity. However, when economic and / or environmental considerations are taken into account, it is preferable to carry out the reaction without using a metal salt.

[0122] The halogenation reaction may be carried out in the presence of a solvent, if necessary. Examples of the solvent include common solvents, such as ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; N , N -dimethylformamide (DMF), N , N -Dimethylacetamide (DMAC), N polar solvents such as N,N'-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), γ-butyrolactone (GBL), acetonitrile, acetone, N,N'-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform; and ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, and n-butyl acetate. From the viewpoint of reactivity, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, dichloromethane, chloroform, γ-butyrolactone, N -Methylpyrrolidone, N , N -dimethylformamide, N , N -Dimethylacetamide and acetonitrile are preferred, and from the viewpoint of safety, 2-methyltetrahydrofuran, γ-butyrolactone and acetonitrile are particularly preferred. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. When a solvent is used in the halogenation reaction, the amount of the solvent used is preferably more than 0 to 3000 g, and more preferably more than 0 to 800 g, per mol of 4,6,8,10-tetramethyltridecanol (7). Since the use of such a solvent reduces the amount of the reaction mixture and decreases the productivity, the reaction may be carried out using a base as a solvent without using the above-mentioned solvent.

[0123] The reaction temperature in the halogenation reaction varies depending on the halogenating agent used, but is preferably 5 to 180°C, more preferably 20 to 120°C, from the viewpoint of reactivity. The reaction time in the halogenation reaction varies depending on the halogenating agent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0124] (iv) 4,6,8,10-tetramethyltridecyl nucleophile (9) and its preparation method A method for producing the above 4,6,8,10-tetramethyltridecyl nucleophilic reagent (9) will be described below. (a) The 4,6,8,10-tetramethyltridecyl nucleophile (9) is described below. The 4,6,8,10-tetramethyltridecyl nucleophile (9) is represented by the following general formula (9). [ka] In the above general formula (9), M 2 Li, MgZ 2 , CuZ 2 Or CuLiZ 2 where Z 2 represents a halogen atom or a 4,6,8,10-tetramethyltridecyl group. 2 Examples of the aryl group include a chlorine atom, a bromine atom, and an iodine atom.

[0125] Specific examples of the 4,6,8,10-tetramethyltridecyl nucleophilic reagent (9) include 4,6,8,10-tetramethyltridecyllithium; 4,6,8,10-tetramethyltridecylmagnesium halide reagents (M), such as 4,6,8,10-tetramethyltridecylmagnesium chloride, 4,6,8,10-tetramethyltridecylmagnesium bromide, and 4,6,8,10-tetramethyltridecylmagnesium iodide. 2 =MgZ 2 (The above are Grignard reagents); Bis[4,6,8,10-tetramethyltridecyl]cuprate (M2 =CuZ 2 In the case of lithium bis[4,6,8,10-tetramethyltridecyl]cuprate, etc., Gillman's reagent (M 2 =CuLiZ 2 (the above are Gilman reagents), and from the viewpoint of reactivity, Grignard reagents such as 4,6,8,10-tetramethyltridecylmagnesium halide reagent are preferred.

[0126] (b) Next, a method for producing the above 4,6,8,10-tetramethyltridecyl nucleophilic reagent (9) will be described below. The 4,6,8,10-tetramethyltridecyl nucleophile (9) can be prepared by conventional methods or as described below.

[0127] [ka]

[0128] For example, 4,6,8,10-tetramethyltridecyl nucleophile (9), M 2 MgZ 2 In the case of 4,6,8,10-tetramethyltridecylmagnesium halide reagent (9:M 2 =MgZ 2 A method for producing ) (i.e., a Grignard reagent) will be described as an example. 4,6,8,10-Tetramethyltridecylmagnesium halide reagent (9:M 2 =MgZ 2 , Z 2 = halogen atom) can be prepared, for example, by reacting the above 1-halo-4,6,8,10-tetramethyltridecane compound (8) with magnesium in a solvent, as shown in the following chemical reaction formula.

[0129] [ka]

[0130] The amount of magnesium used is preferably 1.0 to 2.0 gram atoms per mole of the 1-halo-4,6,8,10-tetramethyltridecane compound (8) from the viewpoint of completing the reaction.

[0131] Examples of the solvent include general solvents, for example, ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; and hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene. From the viewpoint of the reaction rate of the production of the Grignard reagent, preferred are hydrocarbon solvents such as toluene and xylene; and ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran, and more preferred are tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mole of the 1-halo-4,6,8,10-tetramethyltridecane compound (8) from the viewpoint of reactivity.

[0132] The reaction temperature varies depending on the solvent used, but is preferably 30 to 120° C. from the viewpoint of reactivity. The reaction time varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0133] (v) 4,6,8,10,16-pentamethyldocosane (11) and its production method (a) 4,6,8,10,16-pentamethyldocosane (11) is described below. 4,6,8,10,16-Pentamethyldocosane (11) is represented by the following general formula (11). [ka] (b) Next, a method for producing the above 4,6,8,10,16-pentamethyldocosane (11) will be described. For example, 4,6,8,10,16-pentamethyldocosane (11) can be prepared using a 4,6,8,10-tetramethyltridecyl nucleophile represented by the following general formula (9) and a 1-halo-3-methylnonane compound represented by the following general formula (10), as shown in the following chemical reaction formula.

[0134] [ka]

[0135] The process comprises the step of coupling a 4,6,8,10-tetramethyltridecyl nucleophile (9) with a 1-halo-3-methylnonane compound (10).

[0136] The above 1-halo-3-methylnonane compound (10) will be explained below. [ka] In the above general formula (10), X 4 represents a halogen atom. Halogen atom X 4 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of reactivity, a bromine atom and an iodine atom are preferred, and a bromine atom is particularly preferred.

[0137] Specific examples of the 1-halo-3-methylnonane compound (10) include 1-chloro-3-methylnonane, 1-bromo-3-methylnonane, and 1-iodo-3-methylnonane. From the viewpoint of yield, 1-bromo-3-methylnonane and 1-iodo-3-methylnonane are preferred. The 1-halo-3-methylnonane compound (10) may be used alone or, if necessary, in combination of two or more kinds. The 1-halo-3-methylnonane compound (10) may be a commercially available product or may be independently synthesized.

[0138] The 1-halo-3-methylnonane compound (10) can be prepared, for example, by subjecting 3-methylnonanol to a halogenation reaction.

[0139] Next, the coupling reaction of the 4,6,8,10-tetramethyltridecyl nucleophile (9) with the 1-halo-3-methylnonane compound (10) will be described below. In the coupling reaction, the amount of the 4,6,8,10-tetramethyltridecyl nucleophilic reagent (9) used is preferably 0.8 to 1.4 moles per mole of the 1-halo-3-methylnonane compound (10) from the viewpoint of economic efficiency.

[0140] The coupling reaction may be carried out in the presence of a solvent, if necessary. Examples of the solvent include common solvents, such as ether solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, dibutyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; N , N -dimethylformamide (DMF), N , N -Dimethylacetamide (DMAC), N -methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), gamma-butyrolactone (GBL), acetonitrile, N , NExamples of polar solvents include '-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, chloroform, and the like. From the viewpoint of reactivity, however, preferred are hydrocarbon solvents such as toluene and xylene; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran; and acetonitrile; and more preferred are tetrahydrofuran, 2-methyltetrahydrofuran, toluene, and xylene. The solvent may be used alone or in combination with two or more solvents as required. In addition, commercially available solvents may be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mol of the 1-halo-3-methylnonane compound (10) from the viewpoint of reactivity.

[0141] The coupling reaction may be carried out using a catalyst as necessary. Examples of the catalyst include monovalent copper halides such as copper(I) chloride, copper(I) bromide, and copper(I) iodide; and divalent copper halides such as copper(II) chloride, copper(II) bromide, and copper(II) iodide. From the viewpoint of reactivity, the monovalent copper halides are preferred, and copper(I) chloride is more preferred. The catalyst may be used alone or in combination with two or more kinds, if necessary. In addition, commercially available catalysts may be used. The amount of the catalyst used is preferably 0.0003 to 0.3 mol, more preferably 0.001 to 0.1 mol, per mol of the 1-halo-3-methylnonane compound (10), from the viewpoint of reaction rate and / or post-treatment.

[0142] When a catalyst is used in the coupling reaction, a cocatalyst may be used as necessary. Examples of the cocatalyst include phosphorus compounds such as trialkyl phosphite compounds having 3 to 9 carbon atoms, such as triethyl phosphite, and triarylphosphine compounds having 18 to 21 carbon atoms, such as triphenylphosphine, and the like. From the viewpoint of reactivity, trialkyl phosphite compounds are preferred. The co-catalyst may be one type or, if necessary, two or more types. In addition, the co-catalyst may be a commercially available product. The amount of the cocatalyst used is preferably 0.001 to 0.500 mol, more preferably 0.005 to 0.200 mol, per 1 mol of the 1-halo-3-methylnonane compound (10) from the viewpoint of reactivity.

[0143] When a catalyst is used in the coupling reaction, a lithium halide may be added as necessary. Examples of the lithium halide include lithium chloride, lithium bromide, and lithium iodide, and from the viewpoint of reactivity, lithium chloride is preferred. The lithium halide may be one type or, if necessary, two or more types. In addition, the lithium halide may be a commercially available product. The amount of lithium halide used in the coupling reaction is preferably 0.005 to 0.250 mol per 1 mol of the 1-halo-3-methylnonane compound (10) from the viewpoint of reactivity.

[0144] The reaction temperature in the coupling reaction varies depending on the 4,6,8,10-tetramethyltridecyl nucleophilic reagent (9) used, but is preferably −78 to 70° C., more preferably −20 to 50° C., and even more preferably 5 to 35° C., from the viewpoint of reactivity. The reaction time in the coupling reaction varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0145] As described above, according to the present invention, a synthetic intermediate, haloalkyl alkoxymethyl ether compound (2), Antitrogus little boy This method allows the production of 4,6,8,10,16-pentamethyldocosane (11), a cuticular hydrocarbon of the fungus Bacillus subtilis, in a short process with high productivity and efficiency.

[0146] [Example] The present invention will be described in detail below with reference to examples, but the present invention is not limited to the following examples. In the following, unless otherwise specified, "purity" refers to the area percentage obtained by gas chromatography (GC) analysis, "production ratio" refers to the relative ratio of the area percentage obtained by GC analysis, and "yield" was calculated based on the area percentage obtained by GC analysis. In each example, reaction monitoring and yield calculation were performed according to the following GC conditions. GC conditions: GC: Shimadzu Corporation capillary gas chromatograph GC-2014, column: DB-5, 0.25 μm x 0.25 mm φ x 30 m, carrier gas: He (1.55 mL / min), detector: FID, column temperature: 150 ° C. 5 ° C. / min heating to 230 ° C., DB-WAX, 0.25 μm x 0.25 mm φ x 30 m, carrier gas: He (1.55 mL / min), detector: FID, column temperature: 150 ° C. 5 ° C. / min heating to 230 ° C.

[0147] The yield was calculated according to the following formula, taking into account the purity (%GC) of the raw materials and the product. Yield (%) = {[(weight of product obtained by reaction × %GC) / molecular weight of product] ÷[(weight of starting material in reaction × %GC) / molecular weight of starting material]} × 100 In addition, THF represents tetrahydrofuran, GBL represents γ-butyrolactone, PO represents propylene oxide, Ph represents a phenyl group, and Et represents an ethyl group.

[0148] [Example 1] 8-Hydroxy-4,6-dimethylnonyl methoxymethyl ether (4:n+1=3, R 1 =H)

[0149] [ka]

[0150] Magnesium (22.66 g, 0.98 gram atom) and tetrahydrofuran (279.72 g) were added to the reactor at room temperature and stirred at 60-65° C. for 31 minutes. Next, 6-chloro-4-methylheptyl methoxymethyl ether (1:n=2, R 1 =H,X 1 6-Methoxymethoxy-1,3-dimethylhexylmagnesium chloride (2:n=2, R =Cl) (220.00 g, 0.93 mol, purity 88.46%) was added dropwise at 60 to 75°C. After completion of the dropwise addition, the mixture was stirred at 75 to 80°C for 2 hours to obtain 6-methoxymethoxy-1,3-dimethylhexylmagnesium chloride (2:n=2, R =Cl). 1 =H,M 1 = MgCl) was prepared.

[0151] The internal temperature of the reactor was then cooled to 0-10°C, followed by the addition of cuprous chloride (0.19g, 0.0019mol) to the reactor, followed by the dropwise addition of propylene oxide at 5-30°C. After the dropwise addition was completed, the mixture was stirred at 15-25°C for 3 hours. Next, an aqueous solution of acetic acid (acetic acid (127.25g) and water (381.78g)) and hexane (90.49g) were added to the reaction solution to separate the liquid, and the resulting organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 8-hydroxy-4,6-dimethylnonyl methoxymethyl ether (4:n+1=3, R 1 =H) (182.15 g, 0.75 mol, purity 95.28%, bp = 120.0-127.8 °C / 0.36 kPa (2.7 mmHg)) was obtained in a yield of 80.11%.

[0152] The above-obtained 8-hydroxy-4,6-dimethylnonyl methoxymethyl ether (4:n+1=3, R 1 The spectral data for (H) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR(500MHz,CDCl3):δ=0.80-0.90(6H,m),0.90-1.14(2H,m),1.14-1.20(4H,m),1.20 -1.75(8H,m),3.34(3H,s),3.49(2H,t-like,J=6.9Hz),3.83-3.92(1H,m),4.60(2H,s); 13C-NMR (125MHz, CDCl3): δ=19.26,19.31,19.91,20.05,20.14,20.68,23.57,23.78,24.25,26.70,26.87,27.10,27.24, 27.26,29.72,32.81,44.55,44.94,45.23,45.60,46.65,47.67,47.82,55.04,65.59,65.98,66.14,68.13,68.21,96.33 [Mass spectrum] EI-mass spectrum (70 eV): m / z 231 (M + -1), 201, 139, 97, 85, 69, 57, 45, 29 [Infrared absorption spectrum] (D-ATR): ν=2957, 2927, 1461, 1378, 1304, 1214, 1153, 1111, 1045, 920

[0153] [Example 2] 8-Chloro-4,6-dimethylnonyl methoxymethyl ether (1':n+1=3, R 1 =H,X 1 Preparation of (=Cl)

[0154] [ka]

[0155] The reactor was charged with 8-hydroxy-4,6-dimethylnonyl methoxymethyl ether (4:n+1=3, R 1 =H) (85.00 g, 0.35 mol, purity 95.28%), pyridine (41.35 g, 0.52 mol) and GBL (100.00 g) were added and stirred at 10°C for 26 minutes.

[0156] Subsequently, methanesulfonyl chloride (CH3SO2Cl) (47.90 g, 0.42 mol) was added dropwise at 5 to 15°C. After completion of the dropwise addition, the temperature was raised to 60 to 65°C, and the mixture was stirred for 9 hours. After completion of the stirring, water (87.13 g) and hexane (52.28 g) were added and the mixture was separated, and the aqueous layer was removed to obtain an organic layer. The obtained organic layer was washed with an aqueous acetic acid solution (acetic acid (3.67 g), water (45.85 g)), and then washed with an aqueous sodium hydrogen carbonate solution (sodium hydrogen carbonate (1.83 g), water (45.85 g)). The obtained organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 100:0 to 9:1) to obtain 8-chloro-4,6-dimethylnonyl methoxymethyl ether (1':n+1 = 3, R 1 =H,X 1 =Cl) (73.37 g, 0.27 mol, 93.15% purity) was obtained in 78.19% yield.

[0157] The above-obtained 8-chloro-4,6-dimethylnonyl methoxymethyl ether (1':n+1=3, R 1 =H,X 1 The spectral data for (=Cl) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.83-0(6H,m),0.90-1.46(4H,m),1.46-1.90(9H,m),3.35(3H,s),3.50(2H,t,J=6.9Hz),4.06-4.14(1H,m),4.61(2H,s); 13 C-NMR (125MHz, CDCl3): δ=18.60,19.11,19.38,19.80,20.26,25.46,26.01,27.58,27. 69,29.78,29.86,32.67,33.36,33.97,34.43,44.36,44.87,55.07,68.15,68.17,96.37 [Mass spectrum] EI-mass spectrum (70 eV): m / z 249 (M + -1), 236, 219, 205, 188, 151, 137, 123, 109, 83, 69, 45 [Infrared absorption spectrum] (D-ATR): ν=2953, 2928, 1461, 1380, 1214, 1153, 1111, 1045, 920, 677, 616

[0158] The above-obtained 8-chloro-4,6-dimethylnonyl methoxymethyl ether (1':n+1=3, R 1 =H,X 1 =Cl) are haloalkyl alkoxymethyl ether compounds (1'n=2, R 1 =H,X 1 In the following Examples 3 and 7, 8-chloro-4,6-dimethylnonyl methoxymethyl ether (1': n+1 = 3, R 1 =H,X 1 It is described that haloalkyl alkoxymethyl ether compounds (1'n = 3, R = Cl) were used as starting materials, but 1 =H,X 1 =Cl) was used as the starting material.

[0159] [Example 3] 10-Hydroxy-4,6,8-trimethylundecyl methoxymethyl ether (4:n+1=4, R 1 =H)

[0160] [ka]

[0161] Magnesium (0.75 g, 0.031 gram atom) and tetrahydrofuran (8.88 g) were added to a reactor at room temperature and stirred at 60 to 65° C. for 19 minutes. Next, 8-chloro-4,6-dimethylnonyl methoxymethyl ether (1′:n+1=3, R 1 =H,X 18-Methoxymethoxy-1,3,5-trimethyloctylmagnesium chloride (2a: n = 3, R = Cl) (7.97 g, 0.030 mol, purity 93.15%) was added dropwise at 60 to 75°C. After completion of the dropwise addition, the mixture was stirred at 75 to 80°C for 3 hours to obtain 8-methoxymethoxy-1,3,5-trimethyloctylmagnesium chloride (2a: n = 3, R 1 =H,M 1 = MgCl) was prepared.

[0162] The internal temperature of the reactor was then cooled to 0-10°C, and cuprous chloride (0.0062g, 0.000059mol) was added to the reactor, followed by dropwise addition of propylene oxide (1.98g, 0.034mol) at 5-30°C. After completion of the dropwise addition, the mixture was stirred at 15-25°C for 3.5 hours. Next, an aqueous solution of acetic acid (acetic acid (4.04g) and water (32.12g)) and hexane (2.87g) were added to the reaction solution to separate the liquid, and the resulting organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-2:1) to obtain 10-hydroxy-4,6,8-trimethylundecyl methoxymethyl ether (4:n+1=4, R 1 =H) (6.94 g, 0.025 mol, 100% purity) was obtained in 85.45% yield.

[0163] The 10-hydroxy-4,6,8-trimethylundecyl methoxymethyl ether (4:n+1=4, R 1 The spectral data for (H) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.77-1.76(26H,m),3.35(3H,s),3.49(2H,t,J=6.9Hz),3.84-3.93(1H,m),4.61(2H,s); 13 C-NMR(125MHz,CDCl3):δ=19.26,20.05,20.18,20.48,23.50,27.11,27.15,27.19,27.22,27.30, 29.79,29.85,29.88,34.45,44.32,45.54,46.87,47.09,55.05,66.30,68.16,68.18,68.22,96.33 [Mass spectrum] EI-mass spectrum (70 eV): m / z 273 (M + -1), 227, 200, 139, 111, 69, 45 [Infrared absorption spectrum] (D-ATR): ν=3440, 2957, 2925, 1461, 1378, 1214, 1153, 1112, 1045, 920

[0164] [Example 4] 10-Chloro-4,6,8-trimethylundecyl methoxymethyl ether (1':n+1=4, R 1 =H,X 1 Preparation of (=Cl)

[0165] [ka]

[0166] The reactor was charged with 10-hydroxy-4,6,8-trimethylundecyl methoxymethyl ether (4:n+1=4, R 1 =H) (5.64 g, 0.021 mol, purity 100%), pyridine (2.44 g, 0.031 mol) and GBL (15.00 g) were added and stirred at 10°C for 12 minutes.

[0167] Subsequently, methanesulfonyl chloride (CH3SO2Cl) (2.83 g, 0.025 mol) was added dropwise at 5 to 15°C. After completion of the dropwise addition, the temperature was raised to 60 to 65°C, and the mixture was stirred for 8 hours. After completion of the stirring, water (15.15 g) and hexane (13.09 g) were added and the mixture was separated, and the aqueous layer was removed to obtain an organic layer. The obtained organic layer was washed with an aqueous acetic acid solution (acetic acid (0.22 g), water (15.00 g)), and then washed with an aqueous sodium hydrogen carbonate solution (sodium hydrogen carbonate (0.11 g), water (15.00 g)). The obtained organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:0 to 5:1) to obtain 10-chloro-4,6,8-trimethylundecyl methoxymethyl ether (1':n+1=4, R 1 =H,X1 =Cl) (5.56 g, 0.017 mol, purity 90.04%) was obtained in 83.03% yield.

[0168] The 10-chloro-4,6,8-trimethylundecyl methoxymethyl ether (1':n+1=4, R 1 =H,X 1 The spectral data for (=Cl) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.75-1.90(25H,m),3.36(3H,s),3.50(2H,t,J=6.9Hz),4.06-4.15(1H,m),4.61(2H,s); 13 C-NMR (125MHz, CDCl3): δ=19.35,19.78,20.24,20.46,26.27,27.10,27.11,27.22,27. 25,27.31,27.52,27.77,29.79,29.86,29.91,32.98,45.28,55.06,68.18,68.22,96.37 [Mass spectrum] EI-mass spectrum (70 eV): m / z 291 (M + -1), 247, 146, 111, 69, 45 [Infrared absorption spectrum] (D-ATR): ν=2854, 2927, 1460, 1380, 1214, 1153, 1111, 1047, 968, 920, 677, 617

[0169] [Example 5] 8-Chloro-4,6-dimethylnonyl butyloxymethyl ether (1':n+1=3, R 1 =CH2CH2CH3,X 1 Preparation of (=Cl)

[0170] [ka]

[0171] Dibutoxymethane (3.02 g, 0.019 mol) and zinc chloride (0.02 g, 0.00018 mol) were added to a reactor at room temperature and stirred for 4 minutes at 15 to 25° C. Next, acetyl chloride (AcCl) (1.31 g, 0.017 mol) was added dropwise to the reactor at 30 to 40° C. After the dropwise addition was completed, the mixture was stirred at 38 to 42° C. for 4 hours to prepare chloromethyl butyl ether.

[0172] Next, the reactor N , N A mixed solution of 2.49 g, 0.017 mol) of 8-diethylaniline and 3.02 g of 8-chloro-4,6-dimethylnonanol (3.02 g, 0.015 mol, purity 99.26%) was added dropwise at 20 to 30° C. After completion of the dropwise addition, the mixture was stirred at 20 to 30° C. for 19 hours. Next, a 25% by mass aqueous solution of sodium hydroxide (2.52 g) and water (1.60 g) were added to the reaction solution to separate the liquid, and the obtained organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:0 to 9:1) to obtain 8-chloro-4,6-dimethylnonyl butyloxymethyl ether (1':n+1=3, R 1 =CH2CH2CH3,X 1 =Cl) (4.03 g, 0.014 mol, 99.99% purity) was obtained in 94.90% yield.

[0173] The above-obtained 8-chloro-4,6-dimethylnonyl butyloxymethyl ether (1':n+1=3, R 1 =CH2CH2CH3,X 1 The spectral data for (=Cl) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.83-0.89(6H,m),0.92(3H,t,J=7.3Hz),1.00-1.90(17 H,m),3.50(2H,t,J=6.9Hz),3.52(2H,t,J=6.9Hz),4.05-4.14(1H,m),4.66(2H,s); 13C-NMR (125MHz, CDCl3): δ=13.87,19.12,19.37,19.58,19.60,19.80,25.47,26.22,27.17,27.30,27.68,27.80,29.68, 29.79,29.86,31.80,33.39,34.00,34.45,43.62,44.84,45.17,47.34,48.44,48.78,56.63,67.51,68.08,68.13,95.25 [Mass spectrum] EI-mass spectrum (70 eV): m / z 291 (M + -1), 257, 205, 151, 111, 87, 57 [Infrared absorption spectrum] (D-ATR): ν=2958, 2929, 2872, 1459, 1380, 1145, 1115, 1071, 1046, 616

[0174] [Example 6] 8-Chloro-4,6-dimethylnonyl benzyloxymethyl ether (1':n+1=3, R 1 =Ph,X 1 Preparation of (=Cl)

[0175] [ka]

[0176] At room temperature, benzyl chloromethyl ether (2.25 g, 0.013 mol, purity 90%) and toluene (4.0 g) were added to a reactor, and the mixture was stirred for 19 minutes at 15 to 25° C. Next, 8-chloro-4,6-dimethylnonanol (2.95 g, 0.011 mol, purity 78.77%) and N , NA mixture of 1.93 g of 1,000 ml ... 1 =Ph,X 1 =Cl) (4.31 g, 0.011 mol, purity 79.80%) was obtained in 93.60% yield.

[0177] The above-obtained 8-chloro-4,6-dimethylnonyl benzyloxymethyl ether (1':n+1=3, R 1 =Ph,X 1 The spectral data for (=Cl) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.80-1.90(19H,m),3.58(2H,t,J=6.9Hz),4.07-4.16(1H,m),4.61(2H,s),4.77(2H,s),7.34-7.38(5H,m); 13 C-NMR (125MHz, CDCl3): δ=20.27,20.29,25.21,26.02,26.94,27.18,27.58,27.69,27.93,29.70,29.79,32.68,44.34, 45.17,47.34,48.16,56.70,68.41,69.23,69.25,69.49,94.58,94.60,127.62,127.85,127.93,128.38,128.42,137.97 [Mass spectrum] EI-mass spectrum (70 eV): m / z 326 (M + ), 151, 120, 91, 55 [Infrared absorption spectrum] (D-ATR): ν=3031, 2953, 2927, 2872, 1497, 1455, 1379, 1208, 1169, 1113, 1048, 1028, 967, 735, 697, 614

[0178] [Example 7] 4,6,8,10-Tetramethyltridecyl methoxymethyl ether (6:R 1 =H)

[0179] [ka]

[0180] Magnesium (3.49 g, 0.14 gram atom) and tetrahydrofuran (75.13 g) were added to a reactor at room temperature, and the mixture was stirred at 60 to 65° C. for 29 minutes. Next, 8-chloro-4,6-dimethylnonyl methoxymethyl ether (1′:n+1=3, R 1 =H,X 1 8-Methoxymethoxy-1,3,5-trimethyloctylmagnesium chloride (2:n=3, R =Cl) (36.78 g, 0.14 mol, purity 93.15%) was added dropwise at 60 to 75°C. After completion of the dropwise addition, the mixture was stirred at 75 to 80°C for 5 hours to obtain 8-methoxymethoxy-1,3,5-trimethyloctylmagnesium chloride (2:n=3, R =Cl) 1 =H,M 1 = MgCl) was prepared.

[0181] Next, in a separate reactor, cuprous iodide (0.26 g, 0.0014 mol), triethyl phosphite (0.54 g, 0.0033 mol), tetrahydrofuran (162.56 g), and 1-bromo-2-methylpentane (5:X 2 =Br) (21.85 g, 0.13 mol, purity 98.05%) was added, and the mixture was stirred at 15 to 25°C with 8-methoxymethoxy-1,3,5-trimethyloctylmagnesium chloride (2:n=3, R 1 =H,M 1=MgCl) was added dropwise. After completion of the dropwise addition, the mixture was stirred at 15 to 25°C for 2.5 hours. Next, an aqueous acetic acid solution (acetic acid (17.07 g) and water (51.23 g)) and a 25% by mass aqueous sodium hydroxide solution (4.09 g) were added to the reaction solution to separate the liquid, and the resulting organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate = 50:1 to 9:1) to obtain 4,6,8,10-tetramethyltridecyl methoxymethyl ether (6:R 1 =H) (36.09 g, 0.10 mol, 87.02% purity) was obtained in 80.50% yield.

[0182] The 4,6,8,10-tetramethyltridecyl methoxymethyl ether (6:R 1 The spectral data for (H) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR(500MHz,CDCl3):δ=0.76-0.90(16H,m),0.90-1.43(11H,m),1.43-1.7 0(6H,m),1.43-1.70(6H,m),3.50(2H,t,J=6.9Hz),3.03(3H,s),4.62(2H,s); 13 C-NMR (125MHz, CDCl3): δ=14.36,14.41,19.34,19.93,19.97,20.00,20.02,20.12,20.14,20.28,20.30,20.42,20. 66,21.01,27.10,27.20,27.24,27.27,27.31,27.39,29.73,29.76,29.82,33.02,40.56,46.12,55.06,68.22,68.26 [Mass spectrum] EI-mass spectrum (70 eV): m / z 299 (M + -1), 269, 255, 239, 225, 199, 185, 171, 155, 141, 125, 111, 85, 69, 45 [Infrared absorption spectrum] (D-ATR): ν=2956, 2915, 2872, 1461, 1379, 1154, 1112, 1047, 921, 740

[0183] [Example 8] Preparation of 4,6,8,10-tetramethyltridecanol (7)

[0184] [ka]

[0185] 4,6,8,10-Tetramethyltridecyl methoxymethyl ether (6:R 1 =H) (36.09g, 0.10mol, purity 87.02%), methanol (50.50g, 1.58mol) and 20% hydrochloric acid (5.05g, 0.028mol as hydrogen chloride) were charged into a reactor equipped with a distillation column, and the reaction liquid was heated to 60°C and stirred for 1 hour. After stirring was completed, the internal temperature of the reactor was raised to 65-70°C, and a mixture of by-produced dimethoxymethane and methanol was distilled and removed from the distillation column. The reaction liquid during the reaction was sampled, and when the reaction rate reached 100%, water (30.30g) was added and separated, and the aqueous layer was removed to obtain an organic layer. The organic layer obtained was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 9:1) to obtain 4,6,8,10-tetramethyltridecanol (7) (27.19 g, 0.10 mol, purity 97.52%) in a 100% yield.

[0186] The spectral data of the 4,6,8,10-tetramethyltridecanol (7) obtained above is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.76-0.90(16H,m),0.90-1.42(12H,m),1.42-1.66(6H,m),1.42-1.67(6H,m),3.62(2H,t,J=6.9Hz); 13C-NMR (125MHz, CDCl3): δ=14.37,14.42,19.25,19.34,19.94,19.97,20.02,20.06,20.1 2,20.15,20.31,20.35,20.44,20.50,20.64,20.95,27.21,27.24,27.27,27.30,27.39, 29.67, 29.72, 29.76, 29.83, 29.88, 29.98, 30.19, 30.21, 30.37, 32.55, 32.86, 34.11, 38.80, 39.44, 40.56, 44.25, 44.31, 45.08, 45.37, 45.66, 45.89, 46.11, 46.22, 63.43, 63.47 [Mass spectrum] EI-mass spectrum (70 eV): m / z 255 (M + -1), 238, 224, 210, 195, 181, 167, 153, 139, 125, 111, 97, 83, 69, 43, 29 [Infrared absorption spectrum] (D-ATR): νmax = 3325, 2857, 2914, 2871, 1460, 1378, 1058, 739

[0187] [Example 9] 1-Chloro-4,6,8,10-tetramethyltridecane (8:X 3 Preparation of (=Cl)

[0188] [ka]

[0189] 4,6,8,10-Tetramethyltridecanol (7) (21.89 g, 0.083 mol, purity 97.52%) obtained in Example 8, pyridine (9.88 g, 0.12 mol) and GBL (12.48 g) were added to a reactor and stirred at 40° C. for 16 minutes.

[0190] Subsequently, methanesulfonyl chloride (CH3SO2Cl) (11.44 g, 0.10 mol) was added dropwise at 40 to 60°C. After completion of the dropwise addition, the temperature was raised to 60 to 65°C, and the mixture was stirred for 10 hours. After completion of the stirring, water (20.81 g) and hexane (12.49 g) were added and separated, and the aqueous layer was removed to obtain an organic layer. The obtained organic layer was washed with an aqueous acetic acid solution (acetic acid (0.89 g), water (10.95 g)), and subsequently washed with an aqueous sodium hydrogen carbonate solution (sodium hydrogen carbonate (0.44 g), water (10.95 g)). The obtained organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 20:1 to 9:1) to obtain 1-chloro-4,6,8,10-tetramethyltridecane (8:X). 3 =Cl) (21.26 g, 0.076 mol, 98.37% purity) was obtained in 91.40% yield.

[0191] The 1-chloro-4,6,8,10-tetramethyltridecane (8:X 3 The spectral data for (=Cl) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.77-0.90(16H,m),0.90-1.65(15H,m),1.65-1.86(2H,m),3.52(2H,t,J=6.9Hz); 13 C-NMR (125MHz, CDCl3): δ=14.38,14.44,19.26,19.36,19.93,19.95,19.99,20.04,20.11,20.16,20.26,20.38,20.51,20.63,20.94,21.03,27. 25,27.29,27.31,27.32,27.41,29.45,29.51,29.55,29.62,29.75,30.1 4,30.18,33.61,33.79,34.09,38.82,44.34,44.95,45.24,45.51,45.66 [Mass spectrum] EI-mass spectrum (70 eV): m / z 274 (M +), 259, 245, 231, 217, 203, 189, 175, 155, 133, 113, 99, 85, 71, 57, 43, 29 [Infrared absorption spectrum] (D-ATR): νmax = 2957, 2914, 2871, 2844, 1461, 1379, 1158, 970, 726, 656

[0192] [Example 10] Preparation of 4,6,8,10,16-pentamethyldocosane (11)

[0193] [ka]

[0194] Magnesium (1.94 g, 0.080 gram atom) and tetrahydrofuran (70.16 g) were added to the reactor at room temperature and stirred at 60-65° C. for 31 minutes. Next, 1-chloro-4,6,8,10-tetramethyltridecane (8:X) obtained in Example 9 was added to the reactor. 3 4,6,8,10-tetramethyltridecylmagnesium chloride (9:M =Cl) (21.26 g, 0.076 mol, purity 98.37%) was added dropwise at 60 to 75 °C. After completion of the dropwise addition, the mixture was stirred at 75 to 80 °C for 5 hours to obtain 4,6,8,10-tetramethyltridecylmagnesium chloride (9:M 2 = MgCl) was prepared.

[0195] Next, in a separate reactor, cuprous chloride (0.085 g, 0.00086 mol), triethyl phosphite (0.85 g, 0.0014 mol), lithium chloride (0.059 g, 0.0014 mol), tetrahydrofuran (132.71 g), and 1-bromo-3-methylnonane (10:X 4 4,6,8,10-tetramethyltridecylmagnesium chloride (9:M =Br) (16.32 g, 0.072 mol, purity 97.97%) was added and the mixture was stirred at 15 to 25°C. 2=MgCl) was added dropwise. After the completion of the dropwise addition, the mixture was stirred at 20 to 30°C for 2 hours. Next, an aqueous solution of acetic acid (acetic acid (0.77g) and water (20.97g)) and 20% by mass hydrochloric acid (1.59g; 0.0087 moles as hydrogen chloride), then an aqueous solution of 25% by mass sodium hydroxide (1.59g; 0.0099 moles as sodium hydroxide) was added to the reaction liquid to separate the liquids, and the organic layer obtained was directly distilled under reduced pressure to remove low boiling point impurities. Subsequently, the residue was purified by silica gel column chromatography (hexane = 100) to obtain 4,6,8,10,16-pentamethyldocosane (11) (24.29g, 0.062 moles, purity 96.43%) in a yield of 80.86%.

[0196] The spectral data of the 4,6,8,10,16-pentamethyldocosane (11) obtained above is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.78-0.92(22H,m),0.92-1.18(8H,m),1.18-1.40(22H,m),1.40-1.63(4H,m); 13 C-NMR(125MHz,CDCl3):δ=14.14,14.40,14.45,19.33,19.39,19.45,19.73,19.97,20.01,20.05,20.08,20.18,20.21, 20.45,22.72,27.08,27.14,27.26,27.28,27.31,27.35,29.73,29.76,30.37,30.40,31.99,32.77,37.12,45.50,46.21 [Mass spectrum] EI-mass spectrum (70 eV): m / z 380 (M + ), 337, 295, 253, 197, 155, 113, 71, 41 [Infrared absorption spectrum] (D-ATR): ν=2857, 2925, 2871, 2854, 1463, 1378, 1157, 970, 724

[0197] [Example 11] 8-Bromo-4,6-dimethylnonyl methoxymethyl ether (1':n+1=3, R 1 =H,X 1 =Br)

[0198] [ka]

[0199] At room temperature, triphenylphosphine (PPh3) (5.51 g, 0.021 mol) and acetonitrile (CH3CN) (15.45 g) were added to a reactor, and the mixture was stirred at 0 to 10°C for 40 minutes. Next, bromine (Br2) (3.21 g, 0.020 mol) was added dropwise to the reactor at 0 to 10°C. After the dropwise addition was completed, the mixture was stirred at 0 to 10°C for 3 hours. Next, 8-hydroxy-4,6-dimethylnonyl methoxymethyl ether (4:n+1=3, R 1 A mixed solution of 8-bromo-4,6-dimethylnonyl methoxymethyl ether (1':n+1=3, R =H) (3.69 g, 0.015 mol, purity 95.28%) and triethylamine (2.14 g, 0.021 mol) was added dropwise at 0 to 10°C. After completion of the dropwise addition, the mixture was stirred at 15 to 25°C for 20 hours. Next, water (20.00 g) and hexane (6.60 g) were added to the reaction solution to separate the liquid, and the resulting organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-9:1) to obtain 8-bromo-4,6-dimethylnonyl methoxymethyl ether (1':n+1=3, R =H) (3.69 g, 0.015 mol, purity 95.28%) and triethylamine (2.14 g, 0.021 mol). 1 =H,X 1 =Br) (3.38 g, 0.0095 mol, 82.67% purity) was obtained in 62.62% yield.

[0200] The above-obtained 8-bromo-4,6-dimethylnonyl methoxymethyl ether (1':n+1=3, R 1 =H,X 1 The spectral data for Br) is shown below. [Nuclear Magnetic Resonance Spectrum] 1H-NMR (500MHz, CDCl3): δ=0.82-0.90(6H,m),0.90-1.45(4H,m),1.45-1.90(9H, m),3.35(3H,s),3.50(2H,dt,J=1.9Hz,6.7Hz),4.14-4.25(1H,m),4.61(2H,s); 13 C-NMR (125MHz, CDCl3): δ=18.56,19.14,19.42,19.45,19.51,19.81,20.29,2 6.21,26.50,27.09,27.15,27.19,27.29,27.31,28.81,28.87,28.89,29.66, 29.75,29.79,29.84,32.64,33.39,33.94,34.44,43.52,44.25,44.72,45.08,48.09,49.04,49.18,49.54,49.57,49.63,60.25,50.40,55.09,68.16,96.37 〔マススペクトル〕EI-マススペクトル(70eV):m / z 293(M + -1),249,206,151,111,69,45 [Infrared absorption スペクトル] (D-ATR): ν=2953,2925,2872,1457,1380,1214,1152,1111,1045,966,920,625,540

Claims

1. The following general formula (1): 【Chemistry 1】 (In the formula, X １ represents a halogen atom, and R １ (where n represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and n represents an integer from 2 to 7.) The haloalkyl-alkoxymethyl-ether compound represented by the following general formula (2): 【Chemistry 2】 (In the formula, M １ represents Li, MgZ １ , CuZ １ or CuLiZ １ , where Z １ represents a halogen atom or Z ２ , and Z ２ is 【Transformation 3】 Represents, and R １ (And n are as defined above, and the wavy line indicates that the structure beyond it has been omitted.) The (2n+2)-alkoxymethoxyalkyl nucleophile is converted to the (2n+2)-alkoxymethoxyalkyl nucleophile (2) as shown in formula (3): 【Chemistry 4】 By subjecting it to a nucleophilic addition reaction to propylene oxide represented by the following general formula (4): 【Transformation 5】 (In the formula, R １ (And n are as defined above.) A step to obtain a hydroxyalkyl-alkoxymethyl-ether compound represented by, By subjecting the hydroxyalkyl-alkoxymethyl ether compound (4) to halogenation, the following general formula (1') is obtained: 【Transformation 6】 (In the formula, X １ , R １ (And n are as defined above.) A step to obtain a haloalkyl-alkoxymethyl-ether compound represented by the following: A method for producing a haloalkyl-alkoxymethyl-ether compound (1') comprising at least [a specific compound].

2. A method for producing a haloalkyl=alkoxymethyl=ether compound (1':n+1=3) according to claim 1, wherein n is 2 in the haloalkyl=alkoxymethyl=ether compounds (1) and (1').

3. A method for producing a haloalkyl=alkoxymethyl=ether compound (1':n+1=3) according to claim 2, The above haloalkyl-alkoxymethyl ether compound (1':n+1=3) is given by the following general formula (2:n=3): 【Transformation 7】 (In the formula, M １ Li, MgZ １ CuZ １ Or CuLiZ １ This represents Z １ R represents a halogen atom or an 8-alkoxymethoxy-1,3,5-trimethyloctyl group, and １ (This is as defined above.) The 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile is converted to the following general formula (5): 【Transformation 8】 (In the formula, X ２ (This represents a halogen atom.) By subjecting it to a coupling reaction with a 1-halo-2-methylpentane compound represented by the following general formula (6): 【Chemistry 9】 (In the formula, R １ (This is as defined above.) A step to obtain a 4,6,8,10-tetramethyltridecyl=alkoxymethyl=ether compound represented by, By subjecting the 4,6,8,10-tetramethyltridecyl=alkoxymethyl=ether compound (6) to a dealkoxymethylation reaction, the following formula (7) is obtained: 【Chemistry 10】 A step to obtain 4,6,8,10-tetramethyltridecanol represented by, By subjecting the halogenation reaction of 4,6,8,10-tetramethyltridecanol (7) to the following general formula (8): 【Chemistry 11】 (In the formula, X ３ (This represents a halogen atom.) A step to obtain a 1-halo-4,6,8,10-tetramethyltridecane compound (8) represented by, The 1-halo-4,6,8,10-tetramethyltridecane compound (8) is given by the following general formula (9): 【Chemistry 12】 (In the formula, M ２ Li, MgZ ２ CuZ ２ Or CuLiZ ２ This represents Z ２ (This represents a halogen atom or a 4,6,8,10-tetramethyltridecyl group.) It is converted to the 4,6,8,10-tetramethyltridecyl nucleophile represented by the following general formula (10): 【Chemistry 13】 (In the formula, X ４ (This represents a halogen atom.) By subjecting it to a coupling reaction with a 1-halo-3-methylnonane compound represented by the following general formula (11): 【Chemistry 14】 The process of obtaining 4,6,8,10,16-pentamethyldocosane represented by the following steps: A method for producing 4,6,8,10,16-pentamethyldocosane (11), comprising at least [the specified element].

4. The following general formula (1: n=3): 【Chemistry 15】 (In the formula, X １ represents a halogen atom, and R １ (This represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group.) The haloalkyl-alkoxymethyl-ether compound represented by the following general formula (2:n=3): 【Chemistry 16】 (In the formula, M １ Li, MgZ １ CuZ １ Or CuLiZ １ This represents Z １ R represents a halogen atom or an 8-alkoxymethoxy-1,3,5-trimethyloctyl group, and １ (This is as defined above.) The 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile is converted to the following general formula (5): 【Chemistry 17】 (In the formula, X ２ (This represents a halogen atom.) By subjecting it to a coupling reaction with a 1-halo-2-methylpentane compound represented by the following general formula (6): [Chemistry 18] (In the formula, R １ (This is as defined above.) A step to obtain a 4,6,8,10-tetramethyltridecyl=alkoxymethyl=ether compound represented by, By subjecting the 4,6,8,10-tetramethyltridecyl=alkoxymethyl=ether compound (6) to a dealkoxymethylation reaction, the following formula (7) is obtained: 【Chemistry 19】 A step to obtain 4,6,8,10-tetramethyltridecanol represented by, By subjecting the aforementioned 4,6,8,10-tetramethyltridecanol (7) to a halogenation reaction, the following general formula (8) is obtained: 【Chemistry 20】 (In the formula, X ３ (This represents a halogen atom.) A step to obtain a 1-halo-4,6,8,10-tetramethyltridecane compound (8) represented by, The 1-halo-4,6,8,10-tetramethyltridecane compound (8) is given by the following general formula (9): 【Chemistry 21】 (In the formula, M ２ Li, MgZ ２ CuZ ２ Or CuLiZ ２ This represents Z ２ (This represents a halogen atom or a 4,6,8,10-tetramethyltridecyl group.) It is converted to the 4,6,8,10-tetramethyltridecyl nucleophile represented by the following general formula (10): 【Chemistry 22】 (In the formula, X ４ (This represents a halogen atom.) By subjecting it to a coupling reaction with a 1-halo-3-methylnonane compound represented by the following general formula (11): 【Chemistry 23】 The process of obtaining 4,6,8,10,16-pentamethyldocosane represented by the following steps: A method for producing 4,6,8,10,16-pentamethyldocosane (11), comprising at least [the specified element].

5. The following general formula (1'): 【Chemistry 24】 (In the formula, X １ represents a halogen atom, and R １ (where n represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and n represents 2.) Haloalkyl-alkoxymethyl-ether compounds represented by The following general formula (2: n=3): 【Chemistry 25】 (In the formula, M １ Li, MgZ １ CuZ １ Or CuLiZ １ This represents Z １ R represents a halogen atom or an 8-alkoxymethoxy-1,3,5-trimethyloctyl group, and １ (This is as defined above.) The 8-alkoxymethoxy-1,3,5-trimethyloctyl nucleophile is converted to the following general formula (5): 【Chemistry 26】 (In the formula, X ２ (This represents a halogen atom.) By subjecting it to a coupling reaction with a 1-halo-2-methylpentane compound represented by the following general formula (6): 【Chemistry 27】 (In the formula, R １ (This is as defined above.) A step to obtain a 4,6,8,10-tetramethyltridecyl=alkoxymethyl=ether compound represented by, By subjecting the 4,6,8,10-tetramethyltridecyl=alkoxymethyl=ether compound (6) to a dealkoxymethylation reaction, the following formula (7) is obtained: 【Chemistry 28】 A step to obtain 4,6,8,10-tetramethyltridecanol represented by, By subjecting the halogenation reaction of 4,6,8,10-tetramethyltridecanol (7) to the following general formula (8): 【Chemistry 29】 (In the formula, X ３ (This represents a halogen atom.) A step to obtain a 1-halo-4,6,8,10-tetramethyltridecane compound (8) represented by, The 1-halo-4,6,8,10-tetramethyltridecane compound (8) is given by the following general formula (9): 【Transformation 30】 (In the formula, M ２ Li, MgZ ２ CuZ ２ Or CuLiZ ２ This represents Z ２ (This represents a halogen atom or a 4,6,8,10-tetramethyltridecyl group.) It is converted to the 4,6,8,10-tetramethyltridecyl nucleophile represented by the following general formula (10): 【Chemistry 31】 (In the formula, X ４ (This represents a halogen atom.) By subjecting it to a coupling reaction with a 1-halo-3-methylnonane compound represented by the following general formula (11): 【Chemistry 32】 The process of obtaining 4,6,8,10,16-pentamethyldocosane represented by the following steps: A method for producing 4,6,8,10,16-pentamethyldocosane (11), comprising at least [the specified element].

6. The following general formula (1'): 【Transformation 33】 (In the formula, X １ represents a halogen atom, R １ (where n represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and n represents an integer from 2 to 7.) A haloalkyl-alkoxymethyl-ether compound represented by [the specified formula].

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