1-halo-2,6,14-trimethyloctadecane compound and method for producing 5,13,17-trimethylalkane compound using the same

Abstract

To provide: a novel compound that is a synthetic intermediate for efficiently preparing a 5,13,17-trimethylalkane compound; and a process for preparing the compound.SOLUTION: The present invention provides a compound represented by the general formula (1). The present invention further provides a process for preparing a compound (4), the process at least comprising the step of converting a compound (1) into a nucleophilic reagent represented by the general formula (2) and subsequently subjecting it to a coupling reaction with an electrophilic alkyl reagent represented by the general formula (3) to obtain the 5,13,17-trimethylalkane compound represented by the general formula (4). (In the formulas: X1 represents a halogen atom; M1 represents Li or MgZ1, where Z1 represents a halogen atom or a 2,6,14-trimethyloctadecyl group; X2 represents a halogen atom or a CH3-C6H4-SO2-O (TsO) group; and n represents an integer from 14 to 18.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to 1-halo-2,6,14-trimethyloctadecane compounds and to the use thereof. Linepithema humile This invention relates to a method for producing 5,13,17-trimethylalkane compounds, which are nestmate recognition pheromones of the insect. [Background technology]

[0002] The Argentine ant ( Linepithema humile Argentine ants have invaded countries around the world, forming supercolonies and driving out native ants, thereby significantly impacting ecosystems. Furthermore, Argentine ants form a symbiotic relationship with agricultural pests, aphids and scale insects, by obtaining honeydew from these pests in exchange for protecting them from natural enemies. Therefore, biological control using natural enemies is often ineffective in areas with high Argentine ant densities. Furthermore, because they can invade human homes through even the smallest gaps, they also pose a sanitary pest. Until now, Argentine ants have been controlled by spraying insecticides, but this type of conventional insecticide spraying is not only ineffective against Argentine ants but is also undesirable from an environmental perspective. Therefore, biological control methods that minimize the use of insecticides have been investigated, and one method that shows promise is the use of nestmate recognition pheromones (see Non-Patent Documents 1 and 2 below).

[0003] Argentine ant ( Linepithema humileKnown nestmate recognition pheromones of the beetle include 5,13,17-trimethylalkane compounds such as 15-methylpentatriacontane, 17-methylpentatriacontane, 17-methylheptatriacontane, 5,13,17-trimethyltritriacontane, 5,13,17-trimethylpentatriacontane, and 5,13,17-trimethylheptatriacontane. Among these, it has been revealed that 5,13,17-trimethylalkane compounds such as 5,13,17-trimethyltritriacontane, 5,13,17-trimethylpentatriacontane, and 5,13,17-trimethylheptatriacontane, as well as 17-methylalkane compounds such as 17-methylpentatriacontane and 17-methylheptatriacontane, are particularly active (Non-Patent Documents 1, 2, and 3).

[0004] As a method for synthesizing the above-mentioned 5,13,17-trimethylalkane compound, a method for producing it in a yield of 0.84 to 3.17% through a total of 11 steps has been reported (see Non-Patent Document 2 below). For example, 8-bromooctanoic acid is reacted with 2 equivalents of methyl R 9-Bromo-2-nonanone is synthesized by reacting 9-Bromo-2-nonanone with 9-Bromo-2-nonanone. p The carbonyl group in 9-bromo-2-nonanone is acetalized with ethylene glycol in the presence of toluenesulfonic acid to synthesize 2-(7-bromoheptyl)-2-methyl-1,3-dioxolane. The resulting 2-(7-bromoheptyl)-2-methyl-1,3-dioxolane is then reacted with magnesium in tetrahydrofuran to convert it to [7-(2-methyl-1,3-dioxolan-2-yl)heptyl]magnesium bromide. The resulting [7-(2-methyl-1,3-dioxolan-2-yl)heptyl]magnesium bromide is then subjected to a nucleophilic addition reaction with 2-hexanone to synthesize α-butyl-α,2-dimethyl-1,3-dioxolane-2-octanol. The resulting α-butyl-α,2-dimethyl-1,3-dioxolane-2-octanol is then catalyzed with an acid catalyst. p -toluenesulfonic acid in benzene, followed by dehydration with an acid catalystp The acetal is deprotected with water and acetone in the presence of toluenesulfonic acid to synthesize 10-methyl-9-tetradecen-2-one. Next, separately synthesized [3-(2-methyl-1,3-dioxolan-2-yl)propyl]magnesium chloride is subjected to a nucleophilic addition reaction with 10-methyl-9-tetradecen-2-one to synthesize α,2-dimethyl-α-(8-methyl-7-dodecen-1-yl)-1,3-dioxolane-2-butanol. The resulting α,2-dimethyl-α-(8-methyl-7-dodecen-1-yl)-1,3-dioxolane-2-butanol is then reacted with an acid catalyst. p -toluenesulfonic acid in benzene, followed by dehydration with an acid catalyst p The acetal is deprotected with water and acetone in the presence of toluenesulfonic acid to synthesize 6,14-dimethyl-5,13-octadecadien-2-one. Separately, an alkyltriphenylphosphonium bromide compound is deprotonated with n-butyllithium to prepare a triphenylphosphonium alkylide compound. The triphenylphosphonium alkylide compound and the 6,14-dimethyl-5,13-octadecadien-2-one are subjected to a Wittig reaction to synthesize a 5,13,17-trimethylalkatrienes. The resulting 5,13,17-trimethylalkatrienes are then hydrogenated in the presence of a palladium-carbon catalyst to produce the 5,13,17-trimethylalkane compounds. [Prior art documents] [Non-patent literature]

[0005] [Non-Patent Document 1] Neil D Tsutsui et al.,BMC Biology,2009,7,71. [Non-patent document 2] Neil D Tsutsui et al.,J.Chem.Ecol.,2010,36,751-758. [Non-patent document 3] E. Sunamura et al., Insectes Sociaux, 2009, 56, 143-147. [Non-patent document 4] Dennis H. Burns et al.,J. Am. Chem. Soc.,1997,119,2125-2133. Summary of the Invention [Problem to be solved by the invention]

[0006] However, the method for producing 5,13,17-trimethylalkane compounds in Non-Patent Document 2 uses benzene, which is highly toxic to humans, as a solvent, making it unsuitable for industrial use. Furthermore, the use of flammable n-butyllithium and palladium-carbon makes it difficult to commercialize. Additionally, the yields of each step are generally low, and the yields of the Grignard reagent addition reaction and the Wittig reaction are particularly low, ranging from 22 to 45%.

[0007] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a novel compound that is a synthetic intermediate for efficiently producing a 5,13,17-trimethylalkane compound, and a method for producing the novel compound. [Means for solving the problem]

[0008] As a result of extensive research to solve the above problems, the present inventors have found that the 1-halo-2,6,14-trimethyloctadecane compound according to the present invention is a novel compound, and that the 1-halo-2,6,14-trimethyloctadecane compound is a useful intermediate in the production of a 5,13,17-trimethylalkane compound. The present inventors have also found that the use of the 1-halo-2,6,14-trimethyloctadecane compound makes it possible to produce an Argentine ant ( Linepithema humileThe present inventors have discovered a method for efficiently producing 5,13,17-trimethylalkane compounds, which are nestmate recognition pheromones of the beetle, in a short number of steps, and have completed the present invention. Furthermore, the present inventors have found that this method is economical and industrially viable for producing 5,13,17-trimethylalkane compounds.

[0009] According to a first aspect of the present invention, a compound represented by the following general formula (1): [ka] (In the formula, X 1 represents a halogen atom.) The present invention provides a 1-halo-2,6,14-trimethyloctadecane compound represented by the formula:

[0010] According to a second aspect of the present invention, the 1-halo-2,6,14-trimethyloctadecane compound (1) is a compound represented by the following general formula (2): [ka] (In the formula, M 1 is Li or MgZ 1 represents Z 1 represents a halogen atom or a 2,6,14-trimethyloctadecyl group. and then reacting the 2,6,14-trimethyloctadecyl nucleophilic reagent (2) with a compound represented by the following general formula (3): CH3(CH2) n X 2 (3) (In the formula, X 2 is a halogen atom or p -toluenesulfonyloxy group (CH3-C6H6-SO2-O (TsO) group), and n represents an integer of 14 to 18. By a coupling reaction with an alkyl electrophilic reagent (3) represented by the following general formula (4): [ka] (wherein n is as defined above). A step of obtaining a 5,13,17-trimethylalkane compound represented by The present invention provides a method for producing the 5,13,17-trimethylalkane compound (4), which comprises at least the steps of:

[0011] According to a third aspect of the present invention, The following general formula (5): [ka] (In the formula, X 3 represents a halogen atom.) A 1-halo-3,11-dimethylpentadecane compound represented by the following general formula (6): [ka] (In the formula, M 2 is Li or MgZ 1 represents Z 1 represents a halogen atom or a 3,11-dimethylpentadecyl group. and then reacting the 3,11-dimethylpentadecyl nucleophilic reagent with the following general formula (7): [ka] (In the formula, X 4 and X 5 represent halogen atoms which may be the same or different. By a coupling reaction with a 1,3-dihalo-2-methylpropane compound represented by the following general formula (1): [ka] (In the formula, X 1 represents a halogen atom.) a step of obtaining the 1-halo-2,6,14-trimethyloctadecane compound represented by the formula: The present invention provides a method for producing the 1-halo-2,6,14-trimethyloctadecane compound (1), which comprises at least the following steps:

[0012] According to a fourth aspect of the present invention, The following formula (8): [ka] a step of halogenating 3,11-dimethylpentadecanol represented by the formula: The method for producing the 1-halo-2,6,14-trimethyloctadecane compound (1) is further provided.

[0013] According to a fifth aspect of the present invention, The following general formula (9): [ka] (In the formula, X 6 represents a halogen atom.) A 2-halo-10-methyltetradecane compound represented by the following general formula (10): [ka] (In the formula, M 3 is Li or MgZ 1 represents Z 1 represents a halogen atom or a 1,9-dimethyltridecyl group. and then subjecting the 1,9-dimethyltridecyl nucleophilic reagent to an addition reaction with ethylene oxide to obtain the 3,11-dimethylpentadecanol (8). The method for producing the 1-halo-2,6,14-trimethyloctadecane compound (1) is further provided.

[0014] According to a sixth aspect of the present invention, The following formula (11): [ka] a step of halogenating 10-methyl-2-tetradecanol represented by the formula (9) to obtain the 2-halo-10-methyltetradecane compound (9) The method for producing the 1-halo-2,6,14-trimethyloctadecane compound (1) is further provided. [Effects of the Invention]

[0015] According to the present invention, 5,13,17-trimethylalkane compounds can be produced in a short number of steps and in high yield without using expensive raw materials. Furthermore, according to the present invention, novel synthetic intermediates useful for producing 5,13,17-trimethylalkane compounds can be provided. DETAILED DESCRIPTION OF THE INVENTION

[0016] In Section A below, novel compounds, 1-halo-2,6,14-trimethyloctadecane compounds, are described.

[0017] Regarding the 1-halo-2,6,14-trimethyloctadecane compound represented by the following general formula (1): [ka] (In the formula, X 1 represents a halogen atom.)

[0018] Halogen atom X 1 Specific examples of the alkyl group include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of versatility, a chlorine atom and a bromine atom are preferred, and a chlorine atom is particularly preferred.

[0019] Specific examples of the 1-halo-2,6,14-trimethyloctadecane compound (1) include 1-chloro-2,6,14-trimethyloctadecane, 1-bromo-2,6,14-trimethyloctadecane, and 1-iodo-2,6,14-trimethyloctadecane.

[0020] The 1-halo-2,6,14-trimethyloctadecane compound (1) can be produced, for example, according to the chemical reaction formula shown below.

[0021] [ka]

[0022] First, a 1,1-dialkoxy-9-methyltridecane compound (14) is produced by coupling a 1-halo-3-methylheptane compound (16) with a 6,6-dialkoxyhexyl magnesium halide compound (15). Subsequently, the resulting 1,1-dialkoxy-9-methyltridecane compound (14) is hydrolyzed to produce 9-methyltridecanal (13). Next, the resulting 9-methyltridecanal (13) is subjected to an addition reaction with a methyl nucleophile (12) to produce 10-methyl-2-tetradecanol (11). The resulting 10-methyl-2-tetradecanol (11) is halogenated to produce a 2-halo-10-methyltetradecane compound (9). The resulting 2-halo-10-methyltetradecane compound (9) is then converted to a 1,9-dimethyltridecyl nucleophile (10), which is then reacted with ethylene oxide to produce 3,11-dimethylpentadecanol (8). The resulting 3,11-dimethylpentadecanol (8) is then halogenated to produce a 1-halo-3,11-dimethylpentadecanol compound (5). The resulting 1-halo-3,11-dimethylpentadecanol compound (5) is then converted to a 3,11-dimethylpentadecyl nucleophile (6), which is then coupled with a 1,3-dihalo-2-methylpropane compound to produce a 1-halo-2,6,14-trimethyloctadecane compound (1).

[0023] Next, in the following section B, the preparation of 1,1-dialkoxy-9-methyltridecane compound (14), which is a useful intermediate for the preparation of 1-halo-2,6,14-trimethyloctadecane compound (1), is described.

[0024] <b-1>1,1-Dialkoxy-9-methyltridecane Compound (14)

[0025] [ka]

[0026] In general formula (14), R 1 and R 2 are monovalent hydrocarbon groups having 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms, which may be the same or different; or R 1 and R 2 are bonded together R 1 -R 2 represents a divalent hydrocarbon group having 2 to 10 carbon atoms, preferably 2 to 5 carbon atoms. Examples of monovalent hydrocarbon groups having 1 to 15 carbon atoms include linear saturated hydrocarbon groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, and n-dodecyl; branched saturated hydrocarbon groups such as isopropyl, 2-methylpropyl, and 2-methylbutyl; linear unsaturated hydrocarbon groups such as 2-propenyl; branched unsaturated hydrocarbon groups such as 2-methyl-2-propenyl; and cyclic saturated hydrocarbon groups such as cyclopropyl. These hydrocarbon groups may also be isomeric with these groups. Furthermore, some of the hydrogen atoms in these hydrocarbon groups may be substituted with methyl, ethyl, or the like. From the viewpoint of ease of handling, the monovalent hydrocarbon group is preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group. R 1 and R 2 are bonded together R 1 -R 2 Examples of the divalent hydrocarbon group having 2 to 10 carbon atoms include linear saturated hydrocarbon groups such as ethylene, 1,3-propylene, and 1,4-butylene; branched saturated hydrocarbon groups such as 1,2-propylene, 2,2-dimethyl-1,3-propylene, 1,2-butylene, 1,3-butylene, 2,3-butylene, and 2,3-dimethyl-2,3-butylene; linear unsaturated hydrocarbon groups such as 1-vinylethylene; branched unsaturated hydrocarbon groups such as 2-methylene-1,3-propylene; and cyclic hydrocarbon groups such as 1,2-cyclopropylene and 1,2-cyclobutylene. Hydrocarbon groups that are isomers of these groups may also be used. Furthermore, some of the hydrogen atoms of these hydrocarbon groups may be substituted with methyl groups, ethyl groups, or the like. In consideration of reactivity in deprotection and / or ease of purification and availability, the divalent hydrocarbon group is preferably a lower hydrocarbon group (preferably having 2 to 4 carbon atoms) which is highly reactive and from which by-products generated by deprotection can be easily removed by washing with water or concentration. Considering these, particularly preferred examples of the divalent hydrocarbon group include an ethylene group, a 1,2-propylene group, a 1,3-propylene group, a 1,2-butylene group, a 1,3-butylene group, and a 2,3-dimethyl-2,3-butylene group. Specific examples of the 1,1-dialkoxy-9-methyltridecane compound (14) include the following compounds: 1,1-dimethoxy-9-methyltridecane, 1,1-diethoxy-9-methyltridecane, 1,1-dipropyloxy-9-methyltridecane, 1,1-dibutyloxy-9-methyltridecane, 1,1-dipentyloxy-9-methyltridecane, 1,1-dihexyloxy-9-methyltridecane, 1,1-diheptyloxy-9-methyltridecane, 1,1-dioctyloxy-9-methyltridecane, 1,1-dinonyloxy-9-methyltridecane, 1,1-didecyloxy-9-methyltridecane, 2-(8-methyldodecyl)-1,3-dioxolane, and 2-(8-methyldodecyl)-1,3-dioxane.

[0027] <b-2>A method for producing a 1,1-dialkoxy-9-methyltridecane compound (14) by a coupling reaction between a 1-halo-3-methylheptane compound (16) and a 6,6-dialkoxyhexylmagnesium halide compound (15).

[0028] <b-2-1>1-Halo-3-methylheptane compound (16)

[0029] [ka]

[0030] In general formula (16), X 8 represents a halogen atom. Halogen atom X 8 Specific examples of the atom include a chlorine atom, a bromine atom, and an iodine atom, and from the viewpoint of reactivity, a bromine atom and an iodine atom are preferred.

[0031] Specific examples of the 1-halo-3-methylheptane compound (16) include 1-chloro-3-methylheptane, 1-bromo-3-methylheptane, and 1-iodo-3-methylheptane. As the 1-halo-3-methylheptane compound (16), 1-bromo-3-methylheptane and 1-iodo-3-methylheptane are preferred from the viewpoint of reactivity.

[0032] The 1-halo-3-methylheptane compound (16) may be used alone or in combination of two or more, as required. The 1-halo-3-methylheptane compound (16) may be commercially available or may be independently synthesized.

[0033] <b-2-2>6,6-Dialkoxyhexylmagnesium Halide Compound (15)

[0034] [ka] R in general formula (15) 1 and R 2 is as defined in the above general formula (14). In general formula (15), X 7 represents a halogen atom. Halogen atom X 7 Specific examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of ease of handling, a chlorine atom and a bromine atom are preferred, and from the viewpoint of preventing solidification, a chlorine atom is particularly preferred.

[0035] Specific examples of the 6,6-dialkoxyhexyl magnesium halide compound (15) include the following compounds: 6,6-Dimethoxyhexyl magnesium chloride, 6,6-diethoxyhexyl magnesium chloride, 6,6-dipropyloxyhexyl magnesium chloride, 6,6-dibutyloxyhexyl magnesium chloride, 6,6-dipentyloxyhexyl magnesium chloride, 6,6-dihexyloxyhexyl magnesium chloride, 6,6-diheptyloxyhexyl magnesium chloride, 6,6-dioctyloxyhexyl magnesium chloride, 6,6-dinonyloxyhexyl magnesium chloride, and 6,6-didecyloxyhexyl magnesium chloride, [ 5-(1,3-dioxolan-2-yl)pentyl]magnesium chloride and [ 6,6-dialkoxyhexyl magnesium chloride compounds such as 5-(1,3-dioxan-2-yl)pentyl] magnesium chloride (15:X 7 = chlorine atom); 6,6-Dimethoxyhexylmagnesium bromide, 6,6-diethoxyhexylmagnesium bromide, 6,6-dipropyloxyhexylmagnesium bromide, 6,6-dibutyloxyhexylmagnesium bromide, 6,6-dipentyloxyhexylmagnesium bromide, 6,6-dihexyloxyhexylmagnesium bromide, 6,6-diheptyloxyhexylmagnesium bromide, 6,6-dioctyloxyhexylmagnesium bromide, 6,6-dinonyloxyhexylmagnesium bromide, and 6,6-didecyloxyhexylmagnesium bromide, as well as [5-(1,3-dioxolan-2-yl)pentyl]magnesium bromide and [ 6,6-dialkoxyhexyl magnesium bromide compounds such as 5-(1,3-dioxan-2-yl)pentyl] magnesium bromide (15:X 7 = bromine atom); and 6,6-Dimethoxyhexylmagnesium iodide, 6,6-diethoxyhexylmagnesium iodide, 6,6-dipropyloxyhexylmagnesium iodide, 6,6-dibutyloxyhexylmagnesium iodide, 6,6-dipentyloxyhexylmagnesium iodide, 6,6-dihexyloxyhexylmagnesium iodide, 6,6-diheptyloxyhexylmagnesium iodide, 6,6-dioctyloxyhexylmagnesium iodide, 6,6-dinonyloxyhexylmagnesium iodide, and 6,6-didecyloxyhexylmagnesium iodide, as well as [5-(1,3-dioxolan-2-yl)pentyl]magnesium iodide and [ 6,6-dialkoxyhexyl magnesium iodide compounds (15:X) such as 5-(1,3-dioxan-2-yl)pentyl] magnesium iodide 7 = iodine atom).

[0036] The amount of the 6,6-dialkoxyhexyl magnesium halide compound (15) used in the coupling reaction is preferably 0.6 to 2.0 mol, more preferably 0.8 to 1.4 mol, per 1 mol of the 1-halo-3-methylheptane compound (16), from the viewpoint of reactivity.

[0037] The 6,6-dialkoxyhexyl magnesium halide compound (15) may be used alone or, if necessary, in combination of two or more. The 6,6-dialkoxyhexyl magnesium halide compound (15) may be commercially available or may be independently synthesized.

[0038] 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), γ-butyrolactone (GBL), acetonitrile, N , N Examples of suitable solvents include polar solvents such as '-dimethylpropylene urea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform. From the viewpoint of reactivity, however, hydrocarbon solvents such as toluene and xylene; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran; and acetonitrile are preferred, with tetrahydrofuran, 2-methyltetrahydrofuran, toluene, and xylene being more preferred. The solvent may be used alone or in combination with two or more solvents as required. Commercially available solvents may also be used. From the viewpoint of reactivity, the amount of the solvent used is preferably 30 to 8000 g, more preferably 50 to 5000 g, per mole of the 1-halo-3-methylheptane compound (16).

[0039] A catalyst may be used, if necessary, to effect the coupling reaction of the 6,6-dialkoxyhexyl magnesium halide compound (15) with the 1-halo-3-methylheptane compound (16). Examples of the catalyst include copper compounds such as 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; iron compounds such as iron chloride (II), iron chloride (III), iron bromide (II), iron bromide (III), iron iodide (II), iron iodide (III), and iron acetylacetonate (III); silver compounds such as silver chloride, silver nitrate, and silver acetate; titanium tetrachloride, titanium tetrabromide, titanium (IV) methoxide, titanium (IV) ethoxide, titanium (IV) isopropoxide, and titanium oxide (I); palladium(II) compounds such as dichlorobis(triphenylphosphine)palladium and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium; and nickel compounds such as nickel chloride, dichloro[1,2-bis(diphenylphosphino)ethane]nickel(II) and dichlorobis(triphenylphosphine)nickel(II). From the viewpoints of reactivity and / or economy, copper compounds are preferred, and copper (I) halides such as cuprous chloride, cuprous bromide and cuprous iodide are more preferred. The catalyst may be used alone or in combination of two or more types as required. Commercially available catalysts may also be used. The amount of the catalyst used is preferably 0.0001 to 1.00 mol, more preferably 0.001 to 0.300 mol, per 1 mol of the 1-halo-3-methylheptane compound (16), from the viewpoints of reaction rate and post-treatment.

[0040] When a catalyst is used in the coupling reaction, a co-catalyst may be used as necessary. Examples of the co-catalyst include trialkyl phosphite compounds having 3 to 9 carbon atoms, such as triethyl phosphite, and arylphosphine compounds having 18 to 44 carbon atoms, such as triphenylphosphine, tritolylphosphine, and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP). From the viewpoint of reactivity, trialkyl phosphite compounds are preferred, and triethyl phosphite is particularly preferred. The co-catalyst may be used alone or in combination with two or more types as required. Commercially available co-catalysts may also be used. The amount of the cocatalyst used is preferably 0.0001 to 1.00 mol, more preferably 0.001 to 0.300 mol, per 1 mol of the 1-halo-3-methylheptane compound (16).

[0041] When a catalyst is used in the coupling reaction, a lithium salt may be added as needed. Examples of the lithium salt include lithium halides such as lithium chloride, lithium bromide, and lithium iodide; lithium nitrate, and lithium carbonate. From the viewpoint of reactivity, lithium halides such as lithium chloride and lithium nitrate are preferred. The lithium salt may be used alone or in combination with two or more kinds as required. Commercially available lithium salts may be used. In terms of reactivity, the amount of the lithium salt used in the coupling reaction is preferably 0.0001 to 1.00 mol, more preferably 0.001 to 0.300 mol, per 1 mol of the 1-halo-3-methylheptane compound (16).

[0042] The reaction temperature in the coupling reaction varies depending on the 6,6-dialkoxyhexyl magnesium halide compound (15) used, but is preferably −78 to 100° C., more preferably −25 to 60° C., from the viewpoint of reactivity. The reaction time for 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.

[0043] Next, in Section C below, the preparation of 9-methyltridecanal (13) is described.

[0044] <c>A method for producing 9-methyltridecanal (13) by hydrolysis of 1,1-dialkoxy-9-methyltridecane compound (14).

[0045] [ka]

[0046] <c-1>Hydrolysis Reaction In the above hydrolysis reaction, one type of 1,1-dialkoxy-9-methyltridecane compound (14) may be used, or two or more types may be used, as necessary.

[0047] The hydrolysis reaction can be carried out using, for example, an acid and water. Examples of the acid include inorganic acids such as hydrochloric acid and hydrobromic acid; and p-toluenesulfonic acid, benzenesulfonic acid, trifluoroacetic acid, acetic acid, formic acid, oxalic acid, iodotrimethylsilane, and titanium tetrachloride. From the viewpoint of reactivity, acetic acid, formic acid, and oxalic acid are preferred. One or more kinds of the acid may be used, if necessary. In addition, commercially available acids can be used. The amount of the acid used is preferably 0.01 to 10.0 moles per mole of the 1,1-dialkoxy-9-methyltridecane compound (14). The amount of water used is preferably 18 to 7000 g, more preferably 18 to 3000 g, per mole of the 1,1-dialkoxy-9-methyltridecane compound (14) from the viewpoint of reactivity.

[0048] In the hydrolysis reaction, a solvent may be further used in addition to the above-mentioned acid or water, if necessary. Examples of the solvent include 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 Examples of suitable solvents include polar solvents such as dimethylacetamide (DMAC), N-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), γ-butyrolactone (GBL), acetonitrile, acetone, N,N'-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform; ester-based solvents such as methyl acetate, ethyl acetate, n-propyl acetate, and n-butyl acetate; and alcohol-based solvents such as methanol and ethanol. The solvent may be used alone or in combination with two or more solvents as required. Commercially available solvents may also be used. The optimum solvent varies depending on the acid used. For example, when oxalic acid is used as the acid, tetrahydrofuran, 2-methyltetrahydrofuran, acetone and γ-butyrolactone are preferred from the viewpoint of reactivity. The amount of the solvent used is preferably 0 to 7000 g, more preferably 18 to 3000 g, per mole of the 1,1-dialkoxy-9-methyltridecane compound (14) from the viewpoint of reactivity.

[0049] The reaction temperature in the hydrolysis reaction varies depending on the acid and / or solvent used, but is preferably from −15 to 180° C., more preferably from 5 to 120° C., from the viewpoint of reactivity. The reaction time for the hydrolysis reaction varies depending on the acid used, the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours.

[0050] Next, in Section D below, the preparation of 10-methyl-2-tetradecanol (11) is described.

[0051] <d>A method for producing 10-methyl-2-tetradecanol (11) by subjecting 9-methyltridecanal (13) to an addition reaction with a methyl nucleophile (12).

[0052] [ka]

[0053] <d-1>Regarding methyl nucleophiles (12) M in the above general formula (12) 4 Li, MgZ 4 where Z 4 represents a halogen atom or a methyl group. 4 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. Specific examples of the methyl nucleophilic reagent (12) include methyllithium; and methylmagnesium halide reagents (Grignard reagents) such as methylmagnesium chloride, methylmagnesium bromide, and methylmagnesium iodide. From the viewpoint of ease of preparation (versatility), methylmagnesium halide reagents are preferred. The methyl nucleophilic reagent (12) may be used singly or, if necessary, in combination with two or more different methyl nucleophilic reagents (12). The methyl nucleophilic reagent (12) may be commercially available or may be independently synthesized.

[0054] <d-2>The addition reaction of methyl nucleophile (12) to 9-methyltridecanal (13) is described below. In the addition reaction, the amount of the methyl nucleophilic reagent (12) used is preferably 0.8 to 1.2 moles per mole of 9-methyltridecanal (13) from the viewpoint of economy.

[0055] The addition reaction may be carried out in the presence of a solvent, if necessary. Examples of the solvent include 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 Examples of suitable solvents include polar solvents such as dimethylacetamide (DMAC), N-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), γ-butyrolactone (GBL), acetonitrile, N,N'-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform. From the viewpoint of reactivity, however, hydrocarbon solvents such as toluene and xylene are preferred; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran; and acetonitrile are more preferred. The solvent may be used alone or in combination with two or more solvents as required. Commercially available solvents may also be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mole of 9-methyltridecanal (13) from the viewpoint of reactivity.

[0056] The reaction temperature in the addition reaction varies depending on the methyl nucleophilic reagent (12) used, but is preferably −5 to 120° C., more preferably 20 to 100° C., and even more preferably 40 to 80° C., from the viewpoint of reaction yield. The reaction time for the 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.

[0057] Next, in the following section E, the preparation of the 2-halo-10-methyltetradecane compound (9) will be described.

[0058] <e>A method for producing a 2-halo-10-methyltetradecane compound (9) by halogenating 10-methyl-2-tetradecanol (11).

[0059] [ka]

[0060] <e-1>Halogenation reactions The halogenation reaction can be carried out, for example, by p This can be carried out 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, tert -butyldimethylsilyl chloride, tert -butyldimethylsilyl bromide and tert alkylsilyl halide compounds such as butyldimethylsilyl iodide; oxalyl halide compounds such as oxalyl chloride, oxalyl bromide and oxalyl iodide; and N chlorosuccinimide, N -bromosuccinimide and N -iodosuccinimide, etc. N However, 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 types as required. Commercially available halogenating agents may also be used. From the viewpoint of reactivity, the amount of the halogenating agent used is preferably 0.8 to 5.0 mol, more preferably 1.0 to 2.5 mol, per 1 mol of 10-methyl-2-tetradecanol (11).

[0061] 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. One type of base may be used, or two or more types may be used as needed. In addition, commercially available bases can be used. From the viewpoint of yield and / or economy, the amount of the base used is preferably 0 to 8.0 mol, more preferably 0 to 3.0 mol, per 1 mol of 10-methyl-2-tetradecanol (11).

[0062] 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 is carried out using a lithium salt such as lithium chloride, lithium bromide, or lithium iodide. One or more types of the metal salt may be used, if necessary. Commercially available metal salts may also be used. From the viewpoint of reactivity, the amount of the metal salt used is preferably 0 to 30.0 mol, more preferably 0 to 5.0 mol, per 1 mol of 10-methyl-2-tetradecanol (11). By adding the metal salt, the concentration of the halide in the reaction system can be increased, thereby increasing the reactivity. However, taking into account economical and / or environmental considerations, it is preferable to carry out the reaction without using a metal salt.

[0063] The halogenation reaction may be carried out in the presence of a solvent, if necessary. Examples of the solvent include 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 2-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), γ-butyrolactone (GBL), acetonitrile, acetone, N,N'-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, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, dichloromethane, chloroform, γ-butyrolactone, N -methylpyrrolidone, N , N -dimethylformamide, N , N 2-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. Commercially available solvents may also be used. The amount of the solvent used in the halogenation reaction is preferably 0 to 3000 g, more preferably 0 to 800 g, per mole of 10-methyl-2-tetradecanol (11). Since the use of such a solvent reduces the amount of the material to be charged and decreases productivity, the reaction may be carried out using a base as a solvent without using the above solvent.

[0064] 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 for 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.

[0065] <e-2>2-Halo-10-methyltetradecane Compound (9)

[0066] [ka] In the formula, X 6 represents a halogen atom. Halogen atom X 6 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom.

[0067] Specific examples of the 2-halo-10-methyltetradecane compound (9) include 2-chloro-10-methyltetradecane, 2-bromo-10-methyltetradecane, and 2-iodo-10-methyltetradecane.

[0068] Next, in the following section F, the production of 3,11-dimethylpentadecanol (8) is described.

[0069] <f>A method for producing 3,11-dimethylpentadecanol (8) by converting a 2-halo-10-methyltetradecane compound (9) into a 1,9-dimethyltridecyl nucleophile (10), and then subjecting the 1,9-dimethyltridecyl nucleophile (10) to a carbon-promoting reaction with ethylene oxide.

[0070] [ka]

[0071] <f-1>Regarding 1,9-dimethyltridecyl nucleophile (10) The 1,9-dimethyltridecyl nucleophile (10) can be prepared by conventional methods or as described below.

[0072] example As the 1,9-dimethyltridecyl nucleophilic reagent (10), the 1,9-dimethyltridecyl magnesium halide reagent (10:M 3 =MgZ 3 The production method for the case of 1,9-dimethyltridecylmagnesium halide reagent (10:M) is described below. 3 =MgZ 3 ) can be prepared, for example, by reacting the above 2-halo-10-methyltetradecane compound (9) with magnesium in a solvent, as shown in the following chemical reaction formula.

[0073] [ka]

[0074] 1,9-Dimethyltridecylmagnesium halide reagent (10:M 3 =MgZ 3 ) is a Grignard reagent, where Z 3 is X 6 and represents a halogen atom. 6 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom.

[0075] The 2-halo-10-methyltetradecane compound (9) may be used alone or in combination of two or more, as required.

[0076] The amount of magnesium used is preferably 1.0 to 2.0 gram atoms per mole of the 2-halo-10-methyltetradecane compound (9) from the viewpoint of completing the reaction. 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), γ-butyrolactone (GBL), acetonitrile, N , N Examples of suitable solvents include polar solvents such as '-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform. From the viewpoint of the reaction rate of the Grignard reagent production, however, ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, diethyl ether, and 4-methyltetrahydropyran are preferred, and tetrahydrofuran and 2-methyltetrahydrofuran are more preferred. The solvent may be used alone or in combination with two or more solvents as required. Commercially available solvents may also be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mole of the 2-halo-10-methyltetradecane compound (9) from the viewpoint of reactivity.

[0077] The reaction temperature in the reaction with magnesium varies depending on the solvent used, but is preferably 30 to 120°C from the viewpoint of reactivity. The reaction time for the reaction with magnesium varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0078] <f-2>A method for producing 3,11-dimethylpentadecanol (8) by subjecting 1,9-dimethyltridecyl nucleophile (10) to a carbon-promoting reaction with ethylene oxide. From the viewpoint of reactivity, the amount of ethylene oxide used is preferably 1.0 to 10.0 mol, more preferably 1.0 to 5.0 mol, per 1 mol of the 2-halo-10-methyltetradecane compound (9).

[0079] In the carbon-addition reaction, a solvent may be used as needed. 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), γ-butyrolactone (GBL), acetonitrile, N , N Examples of suitable solvents include polar solvents such as '-dimethylpropylene urea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform. From the viewpoint of reactivity, however, ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran, and hydrocarbon solvents such as toluene and xylene are preferred. The solvent may be used alone or in combination with two or more solvents as required. Commercially available solvents may also be used. The amount of the solvent used is preferably 20 to 7000 g, more preferably 50 to 3000 g, per mole of the 2-halo-10-methyltetradecane compound (9) from the viewpoint of reactivity.

[0080] The reaction temperature in the carbon-addition reaction varies depending on the 1,9-dimethyltridecyl nucleophile (10) and / or solvent used, but from the viewpoint of reactivity, it is preferably −40 to 180° C., more preferably −25 to 100° C., and even more preferably −10 to 70° C. The reaction time for the carbon-promoting reaction varies depending on the nucleophilic reagent, solvent and / or reaction scale used, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0081] Next, in the following section G, the production of the 1-halo-3,11-dimethylpentadecane compound (5) will be described.

[0082] <g>A method for producing a 1-halo-3,11-dimethylpentadecanol compound (5) by halogenating 3,11-dimethylpentadecanol (8).

[0083] [ka]

[0084] <g-1>Halogenation reactions The halogenation reaction of 3,11-dimethylpentadecanol (8) is the same as in E-1 above. Note that the amounts of the halogenating agent, base, metal salt, and solvent used in item G are amounts relative to 1 mole of 3,11-dimethylpentadecanol (8).

[0085] Next, in the following section H, the production of the 1-halo-2,6,14-trimethyloctadecane compound (1) will be described.

[0086] <h>A method for producing a 1-halo-2,6,14-trimethyloctadecane compound (1) by converting a 1-halo-3,11-dimethylpentadecane compound (5) into a 3,11-dimethylpentadecyl nucleophile (6), and then coupling the 3,11-dimethylpentadecyl nucleophile with a 1,3-dihalo-2-methylpropane compound (7).

[0087] [ka]

[0088] <h-1>3,11-Dimethylpentadecyl Nucleophile (6) The 3,11-dimethylpentadecyl nucleophile (6) can be prepared by conventional methods or by the methods described below.

[0089] For example, among the 3,11-dimethylpentadecyl nucleophilic reagents (6), the 3,11-dimethylpentadecyl magnesium halide reagent (6:M 2 =MgZ 2 The production method for the case of 3,11-dimethylpentadecyl magnesium halide reagent (6:M) is described below. 2 =MgZ 2 ) can be prepared, for example, by reacting the above-mentioned 1-halo-3,11-dimethylpentadecane compound represented by the following general formula (5) with magnesium in a solvent, as shown in the following chemical reaction formula.

[0090] [ka]

[0091] 3,11-Dimethylpentadecylmagnesium halide reagent (6:M 2 =MgZ 2 ) is a Grignard reagent, where Z 2 is X 3 and represents a halogen atom. 6 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom.

[0092] The 1-halo-3,11-dimethylpentadecane compound (5) may be used alone or, if necessary, in combination with two or more other compounds. The 1-halo-3,11-dimethylpentadecane compound (5) may be a commercially available compound or may be independently synthesized.

[0093] The amount of magnesium used is preferably 1.0 to 2.0 gram atoms per mole of the 1-halo-3,11-dimethylpentadecane compound (5) from the viewpoint of completing the reaction. The solvent, the amount of the solvent used, the reaction temperature and the reaction time are the same as those described in F-1 above.

[0094] <h-2>1,3-Dihalo-2-methylpropane Compound (7) X in the above general formula (7) 4 and X 5 represent halogen atoms which may be the same or different from each other. 4 and X 5 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom. X 4 and X 5 Examples of the combinations include a chlorine atom and a chlorine atom, a bromine atom and a chlorine atom, a chlorine atom and an iodine atom, a bromine atom and a bromine atom, a bromine atom and an iodine atom, and an iodine atom and an iodine atom. Specific examples of the 1,3-dihalo-2-methylpropane compound (7) include 1,3-dichloro-2-methylpropane, 1,3-dibromo-2-methylpropane, 1,3-diiodo-2-methylpropane, 1-bromo-3-chloro-2-methylpropane, 1-chloro-3-iodo-2-methylpropane, and 1-bromo-3-iodo-2-methylpropane. From the viewpoint of yield, 1-bromo-3-chloro-2-methylpropane, 1-chloro-3-iodo-2-methylpropane and 1-bromo-3-iodo-2-methylpropane are particularly preferred. The 1,3-dihalo-2-methylpropane compound (7) may be used alone or, if necessary, in combination with two or more other compounds. The 1,3-dihalo-2-methylpropane compound (7) may be commercially available or may be independently synthesized.

[0095] The 1,3-dihalo-2-methylpropane compound (7) can be synthesized, for example, by halogenating 2-methyl-1,3-propanediol.

[0096] <h-3>Coupling reaction of 3,11-dimethylpentadecyl nucleophile (6) with 1,3-dihalo-2-methylpropane compound (7) In the coupling reaction, the amount of the 3,11-dimethylpentadecyl nucleophilic reagent (6) used is preferably 0.8 to 1.4 moles per mole of the 1,3-dihalo-2-methylpropane compound (7) from the viewpoint of economy.

[0097] The coupling reaction may be carried out in the presence of a solvent, if necessary. Examples of the solvent include 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), γ-butyrolactone (GBL), acetonitrile, acetone, N , N Examples of suitable solvents include polar solvents such as '-dimethylpropylene urea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform. From the viewpoint of reactivity, toluene, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, and acetonitrile are preferred, and tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran are more preferred. The solvent may be used alone or in combination with two or more solvents as required. Commercially available solvents may also be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mole of the 1,3-dihalo-2-methylpropane compound (7) from the viewpoint of reactivity.

[0098] The coupling reaction may be carried out in the presence of a catalyst, if necessary. Examples of the catalyst include copper compounds such as 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; iron compounds such as iron(II) chloride, iron(III) chloride, iron(II) bromide, iron(III) bromide, iron(II) iodide, iron(III) iodide, and iron(III) acetylacetonate; silver compounds such as silver chloride, silver nitrate, and silver acetate; titanium compounds such as titanium tetrachloride, titanium tetrabromide, titanium(IV) methoxide, titanium(IV) ethoxide, titanium(IV) isopropoxide, and titanium(IV) oxide. compounds; palladium(II) compounds such as dichlorobis(triphenylphosphine)palladium and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium; and nickel compounds such as nickel chloride, dichloro[1,2-bis(diphenylphosphino)ethane]nickel(II) and dichlorobis(triphenylphosphine)nickel(II). From the viewpoints of reactivity and / or economy, copper compounds are preferred, copper(I) halides such as cuprous chloride, cuprous bromide and cuprous iodide are more preferred, and cuprous iodide is particularly preferred. The catalyst may be used alone or in combination of two or more types as required. Commercially available catalysts may also be used. The amount of the catalyst used is preferably 0.0001 to 1.00 mol, more preferably 0.001 to 0.300 mol, per 1 mol of the 1,3-dihalo-2-methylpropane compound (7), from the viewpoint of reaction rate and / or post-treatment. When a catalyst is used in the coupling reaction, a co-catalyst may be used as necessary. Examples of the co-catalyst include trialkyl phosphite compounds having 3 to 9 carbon atoms, such as triethyl phosphite, and aryl phosphine compounds having 18 to 44 carbon atoms, such as triphenylphosphine, tritolylphosphine, and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP). From the viewpoint of reactivity, trialkyl phosphite is preferred, and triethyl phosphite is particularly preferred. The co-catalyst may be used alone or in combination with two or more types as required. Commercially available co-catalysts may also be used. The amount of the cocatalyst used is preferably 0.0001 to 1.00 mol, more preferably 0.001 to 0.300 mol, per 1 mol of the 1,3-dihalo-2-methylpropane compound (7) from the viewpoint of reactivity. When a catalyst is used in the coupling reaction, a lithium salt may be added as necessary. Examples of the lithium salt include lithium halides such as lithium chloride, lithium bromide, and lithium iodide, lithium nitrate, and lithium carbonate. From the viewpoint of reactivity, lithium halides such as lithium chloride and lithium nitrate are preferred. One type of lithium salt may be used, or two or more types may be used as needed. In addition, commercially available lithium salts can be used. The amount of the lithium salt used in the coupling reaction is preferably 0.005 to 0.250 moles per mole of the 1,3-dihalo-2-methylpropane compound (7) from the viewpoint of reactivity.

[0099] The reaction temperature in the coupling reaction varies depending on the 3,11-dimethylpentadecyl nucleophilic reagent (6) used, but is preferably −78 to 70° C., more preferably −20 to 35° C., from the viewpoint of reactivity. The reaction time for 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.

[0100] X in the above general formula (7) 4 and X 5 When X are different from each other, the coupling reaction can be carried out while preferentially reacting the more reactive halogen atom by appropriately selecting the catalyst or reaction temperature. 4 and X 5 When a 1,3-dihalo-2-methylpropane compound (7) is used in which the combination of X is a chlorine atom and a bromine atom or a chlorine atom and an iodine atom, the X in the 1-halo-2,6,14-trimethyloctadecane compound (1) can be obtained. 1 can be a chlorine atom. 4 and X 5 If a 1,3-dihalo-2-methylpropane compound (7) is used, in which the combination of X is a bromine atom and an iodine atom, then the X in the 1-halo-2,6,14-trimethyloctadecane compound (1) can be obtained. 1 can be a bromine atom.

[0101] Next, in the following section I, a method for producing a 5,13,17-trimethylalkane compound (4) using a 1-halo-2,6,14-trimethyloctadecane compound (1) will be described. <i-1>The 5,13,17-trimethylalkane compound (4) can be prepared by converting the 1-halo-2,6,14-trimethyloctadecane compound (1) to the 2,6,14-trimethyloctadecyl nucleophile (2), followed by coupling the 2,6,14-trimethyloctadecyl nucleophile (2) with an alkyl electrophile (3).

[0102] [ka]

[0103] <i-2>Method for preparing 2,6,14-trimethyloctadecyl nucleophile (2) The 2,6,14-trimethyloctadecyl nucleophile (2) can be prepared according to conventional methods or according to the method described below.

[0104] <i-3>For example, among the 2,6,14-trimethyloctadecyl nucleophilic reagents (2), the 2,6,14-trimethyloctadecenyl magnesium halide reagent (2:M 1 =MgZ 1 The manufacturing method for the case of ) will be explained below. 2,6,14-Trimethyloctadecenylmagnesium halide reagent (2:M 1 =MgZ 1 ) can be prepared, for example, by reacting the above 1-halo-2,6,14-trimethyloctadecane compound (1) with magnesium in a solvent, as shown in the following chemical reaction formula.

[0105] [ka]

[0106] 2,6,14-Trimethyloctadecenylmagnesium halide reagent (2:M 1 =MgZ 1 ) is a Grignard reagent, where Z 1 is X 1 and represents a halogen atom. 1 As mentioned above, examples of the atom include a chlorine atom, a bromine atom, and an iodine atom.

[0107] The 1-halo-2,6,14-trimethyloctadecane compound (1) may be used alone or in combination with two or more other compounds as required. The 1-halo-2,6,14-trimethyloctadecane compound (1) can be produced, for example, by the methods described in the above paragraphs B to H.

[0108] The amount of magnesium used is preferably 1.0 to 2.0 gram atoms per mole of the 1-halo-2,6,14-trimethyloctadecane compound (1) from the viewpoint of completing the reaction. Examples of the solvent include 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), γ-butyrolactone (GBL), acetonitrile, N , N Examples of suitable solvents include polar solvents such as '-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform. From the viewpoint of the reaction rate of producing the Grignard reagent, ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, diethyl ether, and 4-methyltetrahydropyran are preferred, and tetrahydrofuran and 2-methyltetrahydrofuran are more preferred. The solvent may be used alone or in combination with two or more solvents as required. Commercially available solvents may also 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-2,6,14-trimethyloctadecane compound (1) from the viewpoint of reactivity.

[0109] The reaction temperature in the reaction with magnesium varies depending on the solvent used, but is preferably 30 to 120°C from the viewpoint of reactivity. The reaction time for the reaction with magnesium varies depending on the solvent used and / or the reaction scale, but is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0110] <i-4>Regarding the alkyl electrophile (3) above X in the above general formula (3) 2 is a halogen atom or p -toluenesulfonyloxy group (CH3-C6H6-SO2-O (TsO) group), and n represents an integer of 14 to 18. Halogen atom X 2 Examples of the atom include a chlorine atom, a bromine atom, and an iodine atom, with a bromine atom and an iodine atom being particularly preferred. Specific examples of alkyl electrophiles (3) include the following compounds: 1-halopentadecane compounds such as 1-chloropentadecane, 1-bromopentadecane, and 1-iodopentadecane; Pentadecyl = p -pentadecyl toluenesulfonate, etc.= p -toluenesulfonate compounds; 1-halohexadecane compounds such as 1-chlorohexadecane, 1-bromohexadecane, and 1-iodohexadecane; Hexadecyl = p -Hexadecyl toluenesulfonate, etc. p -toluenesulfonate compounds; 1-haloheptadecane compounds such as 1-chloroheptadecane, 1-bromoheptadecane, and 1-iodoheptadecane; Heptadecyl = p -Heptadecyl toluenesulfonate, etc. p -toluenesulfonate compounds; 1-halooctadecane compounds such as 1-chlorooctadecane, 1-bromooctadecane, and 1-iodooctadecane; Octadecyl = p -Octadecyl toluenesulfonate, etc. p -toluenesulfonate compounds; 1-halononadecane compounds such as 1-chlorononadecane, 1-bromononadecane, and 1-iodononadecane; and Nonadecyl = p -Nonadecyl toluenesulfonate, etc. p -Toluenesulfonate compounds. From the viewpoint of synthesizing nestmate recognition pheromones of Argentine ants, 1-halopentadecane compounds, 1-haloheptadecane compounds and 1-halonadecane compounds are preferred. The alkyl electrophile (3) may be used singly or, if necessary, in combination with two or more different types thereof, and may be commercially available or may be independently synthesized.

[0111] The alkyl electrophile (3) can be prepared, for example, by halogenating a 1-alkanol or by reacting a 1-alkanol with a base. p It can be synthesized by tosylation with -toluenesulfonyl chloride.

[0112] <i-5>Coupling reaction of 2,6,14-trimethyloctadecyl nucleophile (2) with alkyl electrophiles (3) X 2 but p The alkyl electrophile (3), which is a -toluenesulfonyloxy group, is 2 Similarly to alkyl electrophiles (3), where ≡ is a halogen atom, they can be used in the above coupling reactions. p This is because the -toluenesulfonyloxy group serves as a good leaving group, similar to a halogen atom such as a bromine atom (see, for example, page 2127 of the above-mentioned Non-Patent Document 4, "Table 1" and the related descriptions).

[0113] In the coupling reaction, the amount of the 2,6,14-trimethyloctadecyl nucleophilic reagent (2) used is preferably 0.8 to 1.4 moles per mole of the alkyl electrophilic reagent (3) from the viewpoint of economy.

[0114] The coupling reaction may be carried out in the presence of a solvent, if necessary, including 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 Examples of suitable solvents include polar solvents such as dimethylacetamide (DMAC), N-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), γ-butyrolactone (GBL), acetonitrile, N,N'-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, and chloroform. From the viewpoint of reactivity, toluene, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, and acetonitrile are preferred, and tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran are more preferred. The solvent may be used alone or in combination with two or more solvents as required. Commercially available solvents may also be used. The amount of the solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, per mole of the alkyl electrophilic reagent (3) from the viewpoint of reactivity.

[0115] A catalyst may be used in the coupling reaction, if necessary. Examples of the catalyst include copper compounds such as 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; iron compounds such as iron chloride (II), iron chloride (III), iron bromide (II), iron bromide (III), iron iodide (II), iron iodide (III), and iron acetylacetonate (III); silver compounds such as silver chloride, silver nitrate, and silver acetate; titanium compounds such as titanium tetrachloride, titanium tetrabromide, titanium (IV) methoxide, titanium (IV) ethoxide, titanium (IV) isopropoxide, and titanium (IV) oxide. palladium(II) compounds such as dichlorobis(triphenylphosphine)palladium and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium; and nickel compounds such as nickel chloride, dichloro[1,2-bis(diphenylphosphino)ethane]nickel(II) and dichlorobis(triphenylphosphine)nickel(II). From the viewpoint of reactivity and / or economy, copper compounds are preferred, copper(I) halides such as cuprous chloride, cuprous bromide and cuprous iodide are more preferred, and cuprous chloride is particularly preferred. The catalyst may be used alone or in combination of two or more types as required. Commercially available catalysts may also be used. The amount of the catalyst used is preferably 0.0001 to 1.00 mol, more preferably 0.001 to 0.300 mol, per mol of the alkyl electrophilic reagent (3) from the viewpoint of reaction rate and / or post-treatment. When a catalyst is used in the coupling reaction, a co-catalyst may be used as necessary. Examples of the co-catalyst include trialkyl phosphite compounds having 3 to 9 carbon atoms, such as triethyl phosphite, and aryl phosphine compounds having 18 to 44 carbon atoms, such as triphenylphosphine, tritolylphosphine, and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP). From the viewpoint of reactivity, trialkyl phosphite is preferred, and triethyl phosphite is particularly preferred. The co-catalyst may be used alone or in combination with two or more types as required. Commercially available co-catalysts may also be used. The amount of the cocatalyst used is preferably 0.0001 to 1.00 mol, more preferably 0.001 to 0.300 mol, per 1 mol of the alkyl electrophilic reagent (3) from the viewpoint of reactivity.

[0116] When a catalyst is used in the coupling reaction, a lithium salt may be added as necessary. Examples of the lithium salt include lithium halides such as lithium chloride, lithium bromide, and lithium iodide, lithium nitrate, and lithium carbonate. From the viewpoint of reactivity, lithium halides such as lithium chloride and lithium nitrate are preferred. One type of lithium salt may be used, or two or more types may be used as needed. In addition, commercially available lithium salts can be used. From the viewpoint of reactivity, the amount of the lithium salt used in the coupling reaction is preferably 0.0001 to 1.00 mol, more preferably 0.001 to 0.300 mol, per 1 mol of the alkyl electrophilic reagent (3).

[0117] The reaction temperature in the coupling reaction varies depending on the 2,6,14-trimethyloctadecyl nucleophilic reagent (2) used, but is preferably −78 to 100° C., more preferably −20 to 70° C., from the viewpoint of reactivity, and even more preferably 15 to 50° C. from the viewpoint of the melting point of the product, 5,13,17-trimethylalkane compound (4). The reaction time for 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.

[0118] Specific examples of the 5,13,17-trimethylalkane compound (4) include 5,13,17-trimethyltritriacontane (n=14), 5,13,17-trimethyltetratriacontane (n=15), 5,13,17-trimethylpentatriacontane (n=16), 5,13,17-trimethylhexatriacontane (n=17), and 5,13,17-trimethylheptacontane (n=18). Ta Examples include triacontane (n=18).

[0119] In addition to the production method I described above, the 5,13,17-trimethylalkane compound (4) can also be produced by a coupling reaction of a linear alkyl nucleophilic reagent having 15 to 19 carbon atoms, specifically, an alkyllithium compound such as pentadecalithium, heptadecalithium, and nonadecalithium; an alkylmagnesium chloride compound such as pentadecamagnesium chloride, heptadecamagnesium chloride, and nonadecamagnesium chloride; an alkylmagnesium bromide compound such as pentadecamagnesium bromide, heptadecamagnesium bromide, and nonadecamagnesium bromide; or an alkylmagnesium iodide compound such as pentadecamagnesium iodide, heptadecamagnesium iodide, and nonadecamagnesium iodide, with the 1-halo-2,6,14-trimethyloctadecane compound (1).

[0120] As described above, 5,13,17-trimethylalkane compound (4), which is the nestmate recognition pheromone of the Argentine ant, can be produced efficiently in a short process from the synthetic intermediate 1-halo-2,6,14-trimethyloctadecane compound (1).

[0121] [Example] The present invention will be specifically explained below by showing 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 under the following GC conditions. GC conditions: GC: Shimadzu Corporation capillary gas chromatograph GC-2014, column: DB-5 or 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 temperature increase to 230°C.

[0122] 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 Here, THF represents tetrahydrofuran, GBL represents γ-butyrolactone, Ms represents a methanesulfonyl group (CH3SO2), and Et represents an ethyl group.

[0123] Example 1 <1,1-diethoxy-9-methyltridecane (14:R 1 =R 2 =Et) Production>

[0124] [ka]

[0125] At room temperature, a reactor was charged with cuprous chloride (3.04 g, 0.031 moles (mol)), triethyl phosphite (P(OEt)) (30.46 g, 0.18 moles), lithium chloride (2.11 g, 0.050 moles), tetrahydrofuran (271.60 g), and 1-bromo-3-methylheptane (16:X). 8 6,6-diethoxyhexylmagnesium chloride (15:R 1 =R 2 =Et,X 7 A solution of 1,1-diethoxyhexylmagnesium chloride (1447.76 g, 2.72 mol as 6,6-diethoxyhexylmagnesium chloride) in tetrahydrofuran (1447.76 g, 2.72 mol as 6,6-diethoxyhexylmagnesium chloride) was added dropwise. After the addition was completed, the mixture was stirred at 10 to 20°C for 1.5 hours. Next, an aqueous acetic acid solution (acetic acid (339.50 g) and water (1018.50 g)) was added to the reaction mixture, and the mixture was separated. The resulting organic layer was directly distilled under reduced pressure to obtain 1,1-diethoxy-9-methyltridecane (14:R 1 =R 2 =Et) (622.23 g, 2.08 mol, purity 95.63%, bp = 143.2-151.9 °C / 0.4 kPa (3.0 mmHg)) was obtained in a yield of 84.03%.

[0126] The 1,1-diethoxy-9-methyltridecane (14:R 1 =R 2 The spectral data for (Et) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR(500MHz,CDCl3):0.83(3H,d,J=6.9Hz),0.88(3H,t,J=6.9Hz),1.01-1.13(2H,m),1.20(6H,t,J=6.9Hz),1.18-1.37(1 7H,m), 1.60(2H,dt,J=9.0Hz,6.1Hz), 3.48(2H,dq,J=9.4Hz,6.9Hz), 3.63(2H,dq,J=9.4Hz,6.9Hz), 4.50(1H,t,J=5.80Hz); 13 C-NMR (125MHz, CDCl3): δ=14.15,15.34,19.69,23.03,24.76,27.03,29.32,29.49,29.60,29.91,32.70,33.58,36.76,37.05,60.77,102.95 [Mass spectrum] EI-mass spectrum (70 eV): m / z 241 (M + -45), 194, 155, 103, 85, 71, 57, 43, 29 [Infrared absorption spectrum] (D-ATR): νmax = 2954, 2926, 2856, 1485, 1376, 1126, 1063, 1001

[0127] Example 2 <Production of 9-methyltridecanal (13)>

[0128] [ka]

[0129] At room temperature, a reactor was charged with 1,1-diethoxy-9-methyltridecane (14:R 1 =R 2 (=Et) (622.23 g, 2.08 mol, purity 95.63%), oxalic acid dihydrate ((COOH)2) (785.54 g, 6.23 mol), tetrahydrofuran (2077.00 g), and water (2077.00 g) were added and stirred at 60-65°C for 1.5 hours. Hexane (610.85 g) was then added and stirred for 30 minutes. After stirring was completed, the reaction mixture was allowed to stand and separated, and the aqueous layer was removed to obtain an organic layer. The obtained organic layer was then concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 9-methyltridecanal (13) (451.53 g, 2.03 mol, purity 95.51%) in a yield of 97.77%.

[0130] The spectral data of the 9-methyltridecanal (13) obtained above is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.83(3H,d,J=6.5Hz),0.88(3H,t,J=6.9Hz),1.01-1.13(2H,m),1.16-1 .39(15H,m),1.62(2H,quin-like,J=7.3Hz),2.41(2H,dt,J=1.9Hz,7.3Hz),9.76(1H,t,J=1.9Hz); 13 C-NMR (125MHz, CDCl3): δ=14.14,19.67,22.07,23.02,26.96,29.16,29.31,29.38,29.75,32.68,36.74,37.01,43.90,202.93 [Mass spectrum] EI-mass spectrum (70 eV): m / z 212 (M + ), 197, 184, 155, 137, 124, 109, 95, 81, 69, 55, 43, 29 [Infrared absorption spectrum] (D-ATR): νmax = 2955, 2926, 2856, 2713, 1728, 1465, 1378, 727

[0131] Example 3 <Production of 10-methyl-2-tetradecanol (11)>

[0132] [ka]

[0133] At room temperature, a reaction vessel was charged with methylmagnesium chloride (12:M 4 A solution of 9-methyltridecanal (13) (372.89 g, 1.68 mol, purity 95.51%) in tetrahydrofuran (765.82 g, 1.98 mol as methylmagnesium chloride) was added, and the mixture was stirred at 60-65°C for 2 hours. After the dropwise addition, the mixture was stirred at 60-65°C for 2 hours. Next, an aqueous tetrahydrofuran solution (tetrahydrofuran (23.63 g) and water (2.36 g)) was added to the reaction mixture, followed by the addition of an aqueous acetic acid solution (acetic acid (95.92 g) and water (489.62 g)), followed by phase separation. The aqueous layer was then removed to obtain an organic layer. The obtained organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 10-methyl-2-tetradecanol (11) (391.02 g, 1.64 mol, purity 95.74%, bp = 145.1 to 150.0 °C / 0.4 kPa (3.0 mmHg)) in a yield of 97.74%.

[0134] The spectral data of the 10-methyl-2-tetradecanol (11) obtained above is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.83(3H,d,J=6.5Hz),0.88(3H,t,J=6.9Hz),1.02-1.13(2H,m), 1.18(3H,d,J=6.5Hz),1.20-1.32(19H,m),1.56(1H,br.s),3.78(1H,sext-like,J=6.1Hz); 13 C-NMR (125MHz, CDCl3): δ=14.15,19.69,23.03,23.44,25.77,27.04,29.32,29.65,29.93,32.70,36.76,37.05,39.35,68.17 [Mass spectrum] EI-mass spectrum (70 eV): m / z 227 (M + -1), 213, 182, 168, 153, 140, 125, 111, 97, 83, 69, 57, 45, 29 [Infrared absorption spectrum] (D-ATR): νmax = 3350, 2958, 2926, 2855, 1465, 1376, 1119, 940, 725

[0135] Example 4 <2-chloro-10-methyltetradecane (9:X 6 =Cl)

[0136] [ka]

[0137] 10-Methyl-2-tetradecanol (11) (391.02 g, 1.64 mol, purity 95.74%) prepared in Example 3, pyridine (194.47 g, 2.46 mol), and GBL (245.85 g) were added to a reactor at room temperature, and the mixture was stirred at 40° C. for 11 minutes. Subsequently, methanesulfonyl chloride (CHSOCl) (225.30 g, 1.67 mol) was added dropwise at 40-60°C. After the addition was complete, the temperature was raised to 60-65°C and the mixture was stirred for 9 hours. After stirring was complete, water (409.75 g) and hexane (245.85 g) were added and the mixture was separated. The aqueous layer was removed to obtain an organic layer. The obtained organic layer was washed with an aqueous acetic acid solution (acetic acid (18.63 g) and water (232.81 g)), and then with an aqueous sodium bicarbonate solution (sodium bicarbonate (9.31 g) and water (232.81 g)). The obtained organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 2-chloro-10-methyltetradecane (9:X). 6 =Cl) (359.37 g, 1.30 mol, purity 89.52%, bp = 118.8-120.0 °C / 0.4 kPa (3.0 mmHg)) was obtained in a yield of 79.54%.

[0138] The 2-chloro-10-methyltetradecane (9:X 6 The spectral data for (=Cl) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.84(3H,d,J=6.5Hz),0.89(3H,t-like,J=6.9Hz),1.04-1.14(2H,m ),1.18-1.32(17H,m),1.50(3H,d,J=6.5Hz),1.63-1.76(2H,m),4.02(1H,tq,J=6.5Hz,6.5Hz); 13 C-NMR (125MHz, CDCl3): δ=14.16,19.70,23.04,25.34,26.68,27.03,29.14,29.33,29.54,29.91,32.71,36.77,37.05,40.38,58.93 [Mass spectrum] EI-mass spectrum (70 eV): m / z 231 (M + -15), 210, 188, 153, 139, 111, 97, 83, 69, 55, 41, 29 [Infrared absorption spectrum] (D-ATR): νmax = 2955, 2926, 2856, 1465, 1378, 911, 726, 675, 616

[0139] Example 5 <Production of 3,11-dimethylpentadecanol (8)>

[0140] [ka]

[0141] Magnesium (25.33 g, 1.04 mol) and tetrahydrofuran (297.84 g) were added to a reactor at room temperature and stirred at 60 to 65°C for 14 minutes. After stirring was completed, 2-chloro-10-methyltetradecane (9:X) prepared in Example 4 was added to the reactor. 6 1,9-dimethyltridecylmagnesium chloride (10:M = Cl) (273.77 g, 0.99 mol, purity 89.52%) was added dropwise at 60 to 75°C. After the addition was completed, the mixture was stirred at 75 to 80°C for 2.5 hours to obtain 1,9-dimethyltridecylmagnesium chloride (10:M = Cl) 3 = MgCl) was prepared. Next, cuprous chloride (0.21 g, 0.002 mol) was added to the reactor at 0 to 10°C, followed by dropwise addition of ethylene oxide (54.67 g, 1.24 mol) at 0 to 30°C. After completion of the dropwise addition, the reaction mixture was stirred at 0 to 10°C for 2 hours. After completion of the stirring, an aqueous acetic acid solution (acetic acid (124.10 g) and water (372.30 g)) and hexane (88.25 g) were added to the reaction mixture, followed by phase separation. The aqueous layer was removed to obtain an organic layer. The resulting organic layer was then concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 3,11-dimethylpentadecanol (8) (213.50 g, 0.74 mol, purity 88.76%, bp = 135.0 to 142.0°C / 0.4 kPa (3.0 mmHg)) in a yield of 74.43%.

[0142] The spectral data of the 3,11-dimethylpentadecanol (8) obtained above is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.83(3H,d,J=6.9Hz),0.85-0.91(6H,m),1.03-1.15(3H,m),1.16-1.38(22H,m),3.62-3.73(2H,m); 13 C-NMR (125MHz, CDCl3): δ=14.15,19.62,19.69,23.03,26.95,27.07,29.32,29.47,29.73,29.94,30.00,32.71,36.76,37.07,37.13,39.96,61.22 [Mass spectrum] EI-mass spectrum (70 eV): m / z 238 (M + -18), 224, 210, 196, 182, 168, 153, 125, 111, 97, 83, 69, 55, 41 [Infrared absorption spectrum] (D-ATR): νmax = 3334, 2956, 2925, 2855, 1485, 1377, 1058, 724

[0143] Example 6 <1-chloro-3,11-dimethylpentadecane (5:X 3 =Cl)

[0144] [ka]

[0145] 3,11-Dimethylpentadecanol (8) (65.00 g, 0.23 mol, purity 88.76%) prepared in Example 5, pyridine (26.70 g, 0.34 mol), and GBL (33.75 g) were added to a reactor at room temperature, and the mixture was stirred at 40° C. for 26 minutes. Subsequently, methanesulfonyl chloride (CHSOCl) (30.93 g, 0.27 mol) was added dropwise at 40-60°C. After the dropwise addition was completed, the mixture was heated to 60-65°C and stirred for 18 hours. After the stirring was completed, water (56.25 g) and hexane (33.75 g) were added and the mixture was separated. The aqueous layer was removed to obtain an organic layer. The obtained organic layer was washed with an aqueous acetic acid solution (acetic acid (2.37 g) and water (29.61 g)), and then with an aqueous sodium bicarbonate solution (sodium bicarbonate (1.18 g) and water (29.61 g)). The obtained organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 1-chloro-3,11-dimethylpentadecane (5:X). 3 =Cl) (54.64 g, 0.18 mol, purity 90.06%, bp = 125.1-138.0 °C / 0.4 kPa (3.0 mmHg)) was obtained in a yield of 79.56%.

[0146] The 1-chloro-3,11-dimethylpentadecane (5:X 3 The spectral data for (=Cl) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.84(3H,d,J=6.5Hz),0.86-0.91(6H,m),1.12-1.17(3H,m),1.17-1.40 (19H,m)1.53-1.62(1H,m),1.75-1.83(1H,m),3.50-3.62(1H,m),4.03(1H,dt,J=6.5Hz,13.2Hz); 13 C-NMR (125MHz, CDCl3): δ=14.17,19.08,19.71,23.05,26.83,27.08,29.34,29.70,29.87,30.00,30.37,32.72,36.60,36.78,37.08,39.78,43.37 [Mass spectrum] EI-mass spectrum (70 eV): m / z 274 (M + ), 259, 245, 231, 217, 203, 189, 175, 161, 147, 133, 119, 99, 85, 71, 57, 43, 29 [Infrared absorption spectrum] (D-ATR): νmax = 2957, 2925, 2855, 1465, 1378, 1288, 728, 660

[0147] Example 7 <1-chloro-2,6,14-trimethyloctadecane (1:X 1 =Cl)

[0148] [ka]

[0149] Magnesium (4.22 g, 0.17 gram atoms) and tetrahydrofuran (49.62 g) were added to a reactor at room temperature and stirred at 60-65°C for 22 minutes. Next, 1-chloro-3,11-dimethylpentadecane (5:X) prepared in Example 6 was added to the reactor. 3 3,11-dimethylpentadecylmagnesium chloride (6:M = Cl) (50.49 g, 0.17 mol, purity 90.06%) was added dropwise at 60 to 75°C. After the completion of the dropwise addition, the mixture was stirred at 75 to 80°C for 2 hours to obtain 3,11-dimethylpentadecylmagnesium chloride (6:M = Cl) 2 = MgCl) was prepared. Subsequently, in a separate reactor, cuprous iodide (0.31 g, 0.0017 mol), triethyl phosphite (0.66 g, 0.0040 mol), tetrahydrofuran (49.62 g), and 1-bromo-3-chloro-2-methylpropane (7:X 4 =Br, X 5 3,11-dimethylpentadecylmagnesium chloride (6:M) (28.36 g, 0.17 mol) was added, and the resulting mixture was stirred at 5 to 15°C with 3,11-dimethylpentadecylmagnesium chloride (6:M) (28.36 g, 0.17 mol). 2 =MgCl) was added dropwise. After the addition was completed, the mixture was stirred at 10 to 20°C for 2 hours. Next, an aqueous ammonium chloride solution (ammonium chloride (1.65 g) and water (45.57 g)), followed by 20% by mass hydrochloric acid (1.58 g), and finally 25% by mass aqueous sodium hydroxide solution (0.84 g) were added to the reaction mixture, and the mixture was separated. The resulting organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 1-chloro-2,6,14-trimethyloctadecane (1:X 1 =Cl) (48.56 g, 0.14 mol, purity 92.17%, bp = 144.4-160.0 °C / 0.4 kPa (3.0 mmHg)) was obtained in a yield of 81.74%.

[0150] The 1-chloro-2,6,14-trimethyloctadecane (1:X 1 The spectral data for (=Cl) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.82-0.86(6H,m),0.89(3H,t-like,J=6.9Hz),1.00(3H,dd,J=6.5Hz,1.2Hz),1.04-1 .13(4H,m),1.16-1.47(24H,m),1.81(1H,oct-like,J=6.5Hz),3.38-3.43(1H,m),3.48(1H,qd,J=5.4Hz,1.9Hz); 13 C-NMR (125MHz, CDCl3): δ=14.17,17.75,17.82,19.64,19.67,19.71,23.05,24.24,24.26,27.08,27.09,29.34, 29.77,30.02,30.04,32.67,32.68,32.73,34.27,34.29,35.53,36.78,37.02,37.08,37.10,37.12,51.28,51.32 [Mass spectrum] EI-mass spectrum (70 eV): m / z 301 (M + -29)273,211,153,127,111,85,57,41 [Infrared absorption spectrum] (D-ATR): νmax = 2956, 2925, 2854, 1463, 1378, 1261, 730, 688

[0151] Example 8 <Production of 5,13,17-trimethylpentatriacontane (4:n=16)>

[0152] [ka]

[0153] Magnesium (3.31 g, 0.14 gram atom) and tetrahydrofuran (86.50 g) were added to a reactor at room temperature and stirred at 60-65°C for 25 minutes. Next, 1-chloro-2,6,14-trimethyloctadecane (1:X) prepared in Example 7 was added to the reactor. 1 2,6,14-trimethyloctadecylmagnesium chloride (2:M = Cl) (46.64 g, 0.13 mol, purity 92.17%) was added dropwise at 60 to 75°C. After the addition was completed, the mixture was stirred at 75 to 80°C for 4 hours to obtain 2,6,14-trimethyloctadecylmagnesium chloride (2:M = Cl). 1 = MgCl) was prepared. Subsequently, in a separate reactor, cuprous chloride (0.15 g, 0.0015 mol), triethyl phosphite (1.46 g, 0.0088 mol), lithium chloride (0.10 g, 0.0024 mol), tetrahydrofuran (100.00 g), and 1-bromoheptadecane (3:n=16, X 2 2,6,14-trimethyloctadecylmagnesium chloride (2:M) (41.49 g, 0.13 mol) was added to the reaction mixture at 15 to 25°C. 1 = MgCl) was added dropwise. After the addition was completed, the mixture was stirred at 20 to 30°C for 2 hours. Next, an acetic acid aqueous solution (acetic acid (1.30 g) and water (35.79 g)), 20 mass% hydrochloric acid (2.72 g), and 25 mass% sodium hydroxide aqueous solution (2.72 g) were added to the reaction mixture and the mixture was separated. The resulting organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane 100%) to obtain 5,13,17-trimethylpentatriacontane (4:n=16) (63.05 g, 0.11 mol, purity 92.24%) in a yield of 83.68%.

[0154] The spectral data of the 5,13,17-trimethylpentatriacontane (4:n=16) obtained above is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.84(9H,d,J=6.9Hz),0.86-0.92(6H,m),1.01-1.14(6H,m),1.16-1.34(57H,m); 13 C-NMR(125MHz,CDCl3):δ=14.12,14.18,19.70,19.72,19.77,22.71,23.06,24.47,27.11,29.35,29.38, 29.68,29.72,29.75,29.79,30.06,31.94,32.74,32.76,32.78,36.80,37.08,37.12,37.18,37.39,37.44 [Mass spectrum] EI-mass spectrum (70 eV): m / z 519 (M + -15), 477, 351, 281, 252, 211, 169, 141, 113, 85, 57, 29 [Infrared absorption spectrum] (D-ATR): ν=2955, 2923, 2853, 1465, 1379, 721 < / h> < / g> < / f> < / e> < / d> < / c>

Claims

1. The following general formula (1): 【Chemistry 1】 (In the formula, X １ represents a halogen atom.) A 1-halo-2,6,14-trimethyloctadecane compound represented by the formula:

2. The following general formula (1): 【Chemistry 2】 (In the formula, X １ represents a halogen atom.) The 1-halo-2,6,14-trimethyloctadecane compound (1) represented by the following general formula (2): 【Transformation 3】 (In the formula, M １ is Li or MgZ １ represents Z １ represents a halogen atom or a 2,6,14-trimethyloctadecyl group. and then converting the 2,6,14-trimethyloctadecyl nucleophilic reagent (2) into a 2,6,14-trimethyloctadecyl nucleophilic reagent represented by the following general formula (3): CH ３ (CH ２ ) ｎ X ２ (3) (In the formula, X ２ represents a halogen atom or a p-toluenesulfonyloxy group, and n represents an integer of 14 to 18. By a coupling reaction with an alkyl electrophilic reagent (3) represented by the following general formula (4): 【Chemistry 4】 (wherein n is as defined above). A step of obtaining a 5,13,17-trimethylalkane compound represented by The method for producing the 5,13,17-trimethylalkane compound (4) comprises at least

3. The following general formula (5): 【Transformation 5】 (In the formula, X ３ represents a halogen atom.) A 1-halo-3,11-dimethylpentadecane compound represented by the following general formula (6): 【Transformation 6】 (In the formula, M ２ is Li or MgZ １ represents Z １ represents a halogen atom or a 3,11-dimethylpentadecyl group. and then reacting the 3,11-dimethylpentadecyl nucleophilic reagent with the following general formula (7): 【Transformation 7】 (In the formula, X ４ and X ５ represent halogen atoms which may be the same or different. By a coupling reaction with a 1,3-dihalo-2-methylpropane compound represented by the following general formula (1): 【Transformation 8】 (In the formula, X １ represents a halogen atom.) A step of obtaining a 1-halo-2,6,14-trimethyloctadecane compound represented by The method for producing the 1-halo-2,6,14-trimethyloctadecane compound (1) comprises at least:

4. The following formula (8): 【Chemistry 9】 to obtain the 1-halo-3,11-dimethylpentadecanol compound (5). The method for producing the 1-halo-2,6,14-trimethyloctadecane compound (1) according to claim 3, further comprising:

5. The following general formula (9): 【Chemistry 10】 (In the formula, X ６ represents a halogen atom.) The 2-halo-10-methyltetradecane compound represented by the following general formula (10): 【Chemistry 11】 (In the formula, M ３ is Li or MgZ １ represents Z １ represents a halogen atom or a 1,9-dimethyltridecyl group. and then subjecting the 1,9-dimethyltridecyl nucleophile to an addition reaction with ethylene oxide to obtain the 3,11-dimethylpentadecanol (8). The method for producing the 1-halo-2,6,14-trimethyloctadecane compound (1) according to claim 4, further comprising:

6. The following formula (11): 【Chemistry 12】 to obtain the 2-halo-10-methyltetradecane compound (9). The method for producing the 1-halo-2,6,14-trimethyloctadecane compound (1) according to claim 5, further comprising:

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