8-(acyloxy)alkanal compound, process for preparing the same and process for preparing 2,9-diacetoxyundecane from the 8-(acyloxy)alkanal compound

Abstract

To provide a novel synthetic intermediate useful for preparing 2,9-diacetoxyundecane, and a process for preparing the synthetic intermediate, and a method for preparing 2,9-diacetoxyundecane.SOLUTION: The present invention provides a preparation process that comprises the steps of: subjecting a novel synthetic intermediate, 8-(acyloxy)alkanal (1), to a reaction with an alkyl nucleophile reagent of formula (2), thereby obtaining an intermediate (3); and subjecting the intermediate (3) to an acetylation reaction, thereby obtaining 2,9-diacetoxyundecane (4).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an 8-(acyloxy)alkanal compound and a method for producing the same. The present invention also relates to a method for producing 2,9-diacetoxyundecane using the 8-(acyloxy)alkanal compound. The present invention further relates to methods for producing an 8-(acyloxy)nonanal compound, an 8-(acyloxy)decanal compound, and 2,9-diacetoxyundecane using the 8-(acyloxy)alkanal compound. [Background technology]

[0002] Swede midge (scientific name: Contarinia buttons Swede midge is a vegetable pest native to Europe that feeds on Brassica plants such as broccoli and cauliflower. The larvae of the Swede midge secrete a digestive fluid that breaks down the cuticle of the plant, feeding on the leaves and flowers. As a result, the leaves become twisted, curled, wrinkled, or damaged into strings, and the leaf stems become swollen, significantly reducing their commercial value. Since the larvae are protected by the leaves, regular pesticides are often ineffective due to poor contact, making control difficult. In addition, due to concerns about residual pesticides, biological control methods are gaining attention, and one promising method is the use of sex pheromone substances (Non-Patent Document 1 below).

[0003] The sex pheromone composition of the Swede midge is (2 S ,9 S )-2,9-diacetoxyundecane, (2 S ,10 S )-2,10-diacetoxyundecane and (2 S It has been reported that the acetoxyacyl ether is a 1:2:0.02 mixture of acetoxyacyl ether and 2-acetoxyundecane (Non-Patent Document 2 listed below).

[0004] The above (2 S ,9 SAs a method for producing 2,9-diacetoxyundecane, for example, the following method has been reported, which involves a total of seven steps and produces the compound with a yield of 21.39% (Non-Patent Document 2 below). In this method, 7-bromo-1-heptene is used as a starting material, which is reacted with magnesium in tetrahydrofuran (THF) to prepare 6-heptenylmagnesium bromide, which is then subjected to a nucleophilic addition reaction with propylene oxide in the presence of a copper catalyst to produce (2 S The method includes preparing 9-decen-2-ol. S )-9-Decen-2-ol was reacted with sodium hydride in the presence of tetrabutylammonium iodide in tetrahydrofuran, followed by reaction with benzyl bromide to give (2 S )-2-benzyloxy-9-decene is then prepared. S )-2-benzyloxy-9-decene containing water third By reacting with AD-mix-β in 2-butyl alcohol, R ,9 S )-9-(benzyloxy)-1,2-decanediol is then prepared. R ,9 S )-9-(benzyloxy)-1,2-decanediol in pyridine p -toluenesulfonyl chloride to give (2 R ,9 S )-1-(4-methylbenzenesulfonate)-9-(benzyloxy)-1,2-decanediol is then prepared. R ,9 S )-1-(4-methylbenzenesulfonate)-9-(benzyloxy)-1,2-decanediol was reacted with methylmagnesium chloride in tetrahydrofuran to give (3 S ,10 S )-10-(benzyloxy)-3-undecanol was then prepared, and the resulting (3 S ,10 S)-10-(benzyloxy)-3-undecanol is reacted with hydrogen in the presence of palladium on carbon in ethanol to give (2 S ,9 S )-2,9-undecanediol is prepared. S ,9 S The above-mentioned (2)-2,9-undecanediol was acetylated with acetic anhydride in the presence of pyridine and 4-dimethylaminopyridine (DMAP) to give the target compound. S ,9 S )-2,9-Diacetoxyundecane is prepared. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2019-189535 A [Non-patent literature]

[0006] [Non-Patent Document 1] Elisabeth A. Hodgdon et al.,The Canadian Entomologist,2022,154,e37,1-17. [Non-Patent Document 2] Ylva Hillbur et al., J. Chem. Ecol., 2005, 31(8), 1807-1828. Summary of the Invention [Problem to be solved by the invention]

[0007] However, the manufacturing method of Non-Patent Document 2 is not suitable for industrial production because it uses a large amount of highly toxic and expensive AD-mix-β, 5 times the amount of the raw material. Here, AD-mix-β is a mixture composed of expensive hydroquinidine-1,4-phthalazinediyl diether, potassium carbonate, potassium ferricyanide, highly toxic potassium osmate dihydrate, etc. In addition, the manufacturing method of Non-Patent Document 2 is not suitable for industrial production because it uses palladium carbon, which has a risk of ignition. Furthermore, the manufacturing method of Non-Patent Document 2 is not suitable for industrial production because it has many steps and a low yield.

[0008] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a novel synthetic intermediate useful for producing 2,9-diacetoxyundecane, and a method for producing the synthetic intermediate. Another object of the present invention is to provide an efficient method for producing 2,9-diacetoxyundecane using the synthetic intermediate, preferably an efficient and economical method, particularly a method suitable for industrial production. [Means for solving the problem]

[0009] As a result of intensive research conducted by the present inventors to solve the above problems, the present inventors have found that a key intermediate capable of synthesizing 2,9-diacetoxyundecane is a novel 8-(acyloxy)alkanal compound. The present inventors have further found a method for producing the novel 8-(acyloxy)alkanal compound, particularly an inexpensive and efficient method, and a method for producing 2,9-diacetoxyundecane, the sex pheromone of the Swedish midge, from the 8-(acyloxy)alkanal compound, particularly an efficient method for producing the 2,9-diacetoxyundecane, thereby completing the present invention. The present inventors have also found that the above-mentioned method for producing the 8-(acyloxy)alkanal compound and the above-mentioned method for producing the 2,9-diacetoxyundecane are suitable for industrially producing these compounds.

[0010] According to a first aspect of the present invention, there is provided a compound represented by the following general formula (1): [ka] (In the formula, n represents 0 or 1, and R 1 represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which a hydrogen atom is substituted with one or more halogen atoms. The present invention provides an 8-(acyloxy)alkanal compound represented by the formula:

[0011] According to a second aspect of the present invention, the 8-(acyloxy)alkanal compound (1) is represented by the following general formula (2): CH3(CH2) (1-n) M 1 (2) (In the formula, M 1 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 and n represents 0 or 1, where Z 1 represents a halogen atom, a methyl group, or an ethyl group. By subjecting the compound to a nucleophilic addition reaction with an alkyl nucleophilic reagent represented by the following formula (3): [ka] and obtaining 2,9-undecanediol represented by the formula: The 2,9-undecanediol (3) is subjected to an acetylation reaction to obtain a compound represented by the following formula (4): [ka] and obtaining 2,9-diacetoxyundecane represented by the formula: The present invention provides a method for producing the above-mentioned 2,9-diacetoxyundecane (4), comprising at least the steps of:

[0012] According to a third aspect of the present invention, there is provided a compound represented by the following general formula (5): [ka] (In the formula, n represents 0 or 1; R 3 and R 4 are each independently a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R 3 and R 4 are bonded together R 3 -R 4 represents a divalent hydrocarbon group having 2 to 10 carbon atoms, and R 1 is as defined above.) A step of obtaining the 8-(acyloxy)alkanal compound (1) by subjecting a dialkoxyacyloxyalkane compound represented by the following formula (1): The present invention provides a method for producing the above 8-(acyloxy)alkanal compound (1), which comprises at least the steps of:

[0013] According to a fourth aspect of the present invention, there is provided a compound represented by the following general formula (6): [ka] (In the formula, X represents a halogen atom, R 3 and R 4 are each independently a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R 3 and R 4 are bonded together R 3 -R 4 represents a divalent hydrocarbon group having 2 to 10 carbon atoms. The 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (7): [ka] (In the formula, M 2 Li, MgZ 2 , CuZ 2 Or CuLiZ 2 where Z 2 represents a halogen atom or a 6,6-dialkoxyhexyl group, and R 3 and R 4 is as defined above.) and converting the 6,6-dialkoxyhexyl nucleophile (7) into a 6,6-dialkoxyhexyl nucleophile represented by the following formula (8): [ka] By nucleophilic addition reaction to propylene oxide represented by the following general formula (9A): [ka] (In the formula, R 3 and R 4 is as defined above.) obtaining a 9,9-dialkoxy-2-nonanol compound represented by the formula: The 9,9-dialkoxy-2-nonanol compound (9A) is subjected to an acylation reaction to obtain a compound represented by the following general formula (5A): [ka] (In the formula, R 1 ,R 3 and R 4 is as defined above.) obtaining a 9,9-dialkoxy-2-acyloxynonane compound represented by the formula: the 9,9-dialkoxy-2-acyloxynonane compound (5A) is subjected to a hydrolysis reaction to obtain an 8-(acyloxy)alkanal compound (1) (herein, also referred to as "8-(acyloxy)nonanal compound (1:n=0)" or "8-(acyloxy)nonanal compound (1) (wherein n=0)") according to the third embodiment; The present invention provides a method for producing an 8-(acyloxy)alkanal compound (1) (wherein n=0), comprising at least the steps of:

[0014] According to a fifth aspect of the present invention, there is provided a compound represented by the following general formula (6): [ka] (In the formula, X represents a halogen atom, R 3 and R 4are each independently a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R 3 and R 4 are bonded together R 3 -R 4 represents a divalent hydrocarbon group having 2 to 10 carbon atoms. The 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (7): [ka] (In the formula, M 2 Li, MgZ 2 , CuZ 2 Or CuLiZ 2 where Z 2 represents a halogen atom or a 6,6-dialkoxyhexyl group, and R 3 and R 4 is as defined above.) and converting the 6,6-dialkoxyhexyl nucleophile (7) into a 6,6-dialkoxyhexyl nucleophile represented by the following formula (10): [ka] By nucleophilic addition reaction to 1,2-butylene oxide represented by the following general formula (9B): [ka] (In the formula, R 3 and R 4 is as defined above.) obtaining a 10,10-dialkoxy-3-decanol compound represented by the formula: The 10,10-dialkoxy-3-decanol (9B) is subjected to an acylation reaction to obtain a compound represented by the following general formula (5B), in which n is 1 in the above general formula (5): [ka] (In the formula, R 1 ,R 3 and R 4 is as defined above.) obtaining a 10,10-dialkoxy-3-acyloxydecane compound represented by the formula: the 10,10-dialkoxy-3-acyloxydecane compound (5B) is subjected to a hydrolysis reaction to obtain an 8-(acyloxy)alkanal compound (1) (herein, also referred to as "8-(acyloxy)nonanal compound (1:n=1)" or "8-(acyloxy)decanal compound (1) (wherein n=1)") represented by the general formula (1), in which n is 1; The present invention provides a method for producing the above 8-(acyloxy)alkanal compound (1) (wherein n=1), which comprises at least the steps of:

[0015] According to a sixth aspect of the present invention, a process for producing an 8-(acyloxy)alkanal compound (1) from the dialkoxyacyloxyalkane compound (5) according to the third embodiment; a process for producing 2,9-diacetoxyundecane (4) from said 8-(acyloxy)alkanal compound (1) according to the second embodiment; The method for producing 2,9-diacetoxyundecane (4) is provided, which comprises at least

[0016] According to a seventh aspect of the present invention, there is provided a compound represented by the following general formula (6): [ka] (In the formula, X represents a halogen atom, R 3 and R 4 are each independently a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R 3 and R 4 are bonded together R 3 -R 4 represents a divalent hydrocarbon group having 2 to 10 carbon atoms. The 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (7): [ka] (In the formula, M 2Li, MgZ 2 , CuZ 2 Or CuLiZ 2 where Z 2 represents a halogen atom or a 6,6-dialkoxyhexyl group, and R 3 and R 4 is as defined above.) and converting the 6,6-dialkoxyhexyl nucleophile (7) into a 6,6-dialkoxyhexyl nucleophile represented by the following formula (8): [ka] By nucleophilic addition reaction to propylene oxide represented by the following general formula (9A): [ka] (In the formula, R 3 and R 4 is as defined above.) obtaining a 9,9-dialkoxy-2-nonanol compound represented by the formula: The 9,9-dialkoxy-2-nonanol compound (9A) is subjected to an acylation reaction to obtain a compound represented by the following general formula (5A): [ka] (In the formula, R 1 ,R 3 and R 4 is as defined above.) obtaining a 9,9-dialkoxy-2-acyloxynonane compound represented by the formula: a step of subjecting the 9,9-dialkoxy-2-acyloxynonane compound (5A) to a hydrolysis reaction to obtain an 8-(acyloxy)alkanal compound (1) (wherein n=0) represented by the above general formula (1); obtaining 2,9-diacetoxyundecane (4) from the 8-(acyloxy)alkanal compound (1) (wherein n=0), according to the production method described in the second embodiment above; The method for producing 2,9-diacetoxyundecane (4) is provided, which comprises at least

[0017] According to an eighth aspect of the present invention, a compound represented by the following general formula (6): [ka] (In the formula, X represents a halogen atom, R 3 and R 4 are each independently a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R 3 and R 4 are bonded together R 3 -R 4 represents a divalent hydrocarbon group having 2 to 10 carbon atoms. The 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (7): [ka] (In the formula, M 2 Li, MgZ 2 , CuZ 2 Or CuLiZ 2 where Z 2 represents a halogen atom or a 6,6-dialkoxyhexyl group, and R 3 and R 4 is as defined above.) and converting the 6,6-dialkoxyhexyl nucleophile (7) into a 6,6-dialkoxyhexyl nucleophile represented by the following formula (10): [ka] By nucleophilic addition reaction to 1,2-butylene oxide represented by the following general formula (9B): [ka] (In the formula, R 3 and R 4 is as defined above.) obtaining a 10,10-dialkoxy-3-decanol compound represented by the formula: The 9,9-dialkoxy-2-nonanol compound (9B) is subjected to an acylation reaction to obtain a compound represented by the following general formula (5B): [ka] (In the formula, R 1 ,R 3 and R 4 is as defined above.) obtaining a 9,9-dialkoxy-2-acyloxydecane compound represented by the formula: a step of subjecting the 9,9-dialkoxy-2-acyloxydecane compound (5B) to a hydrolysis reaction to obtain an 8-(acyloxy)alkanal compound (1) (wherein n is 1 in the above general formula (1) (also referred to as "n=1"); obtaining 2,9-diacetoxyundecane (4) from the 8-(acyloxy)alkanal compound (1) (wherein n=1), according to the production method described in the second embodiment above; The method for producing 2,9-diacetoxyundecane (4) is provided, which comprises at least Effect of the Invention

[0018] According to the present invention, it is possible to produce an 8-(acyloxy)alkanal compound, which is a synthetic intermediate capable of efficiently synthesizing 2,9-diacetoxyundecane. In addition, by using the 8-(acyloxy)alkanal compound as a key intermediate, it is possible to efficiently produce 2,9-diacetoxyundecane in a short process with less environmental impact. The production method is also economical. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] I. 8-(acyloxy)alkanal compounds represented by the following general formula (1) First, the 8-(acyloxy)alkanal compound (1) will be described.

[0020] [ka]

[0021] In the above general formula (1), n ​​represents 0 or 1. In this specification, when n is 0, it is represented as an 8-(acyloxy)alkanal compound (1:n=0) or an 8-(acyloxy)alkanal compound (1A), and when n is 1, it is represented as an 8-(acyloxy)alkanal compound (1:n=1) or an 8-(acyloxy)alkanal compound (1B). In the above general formula (1), R 1 represents a straight-chain or branched alkyl group having 1 to 10 carbon atoms, preferably 1 to 6, and more preferably 1, 2, 3, or 4 carbon atoms, or a phenyl group or a phenyl group in which a hydrogen atom is substituted with one or more halogen atoms. The linear or branched alkyl group R having 1 to 10 carbon atoms 1 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an isopropyl group, dry -butyl group and third -butyl group. In the phenyl group in which hydrogen atoms are replaced by one or more halogen atoms, the halogen atoms include fluorine, chlorine, bromine and iodine atoms. Any hydrogen atom on the phenyl group can be replaced by a halogen atom. The number of halogen atoms on the phenyl group is 1, 2, 3, 4 or 5. When multiple hydrogen atoms on the phenyl group are replaced by halogen atoms, the halogen atoms can be the same or different.

[0022] Specific examples of the 8-(acyloxy)alkanal compound (1) are described below with respect to an 8-(acyloxy)alkanal compound (1A) and an 8-(acyloxy)alkanal compound (1B). In the case of the 8-(acyloxy)alkanal compound (1A), the following compounds can be mentioned: 8-(Acyloxy)nonanal compounds such as 8-(acetyloxy)nonanal, 8-(propionyloxy)nonanal, 8-(butyryloxy)nonanal, 8-(isobutyryloxy)nonanal, 8-(2-methylbutyryloxy)nonanal, 8-(pivaloyloxy)nonanal and 8-(benzoyloxy)nonanal. In the case of the 8-(acyloxy)alkanal compound (1B), the following compounds can be mentioned: 8-(Acyloxy)decanal compounds such as 8-(acetyloxy)decanal, 8-(propionyloxy)decanal, 8-(butyryloxy)decanal, 8-(isobutyryloxy)decanal, 8-(2-methylbutyryloxy)decanal, 8-(pivaloyloxy)decanal and 8-(benzoyloxy)decanal.

[0023] II. Method for producing the above 8-(acyloxy)alkanal compound (1) An 8-(acyloxy)alkanal compound (1), which is one of the target compounds of the present invention, can be produced, for example, from a 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (6) according to the production method shown in the following chemical reaction scheme.

[0024] [ka]

[0025] That is, the 8-(acyloxy)alkanal compound (1) can be produced by (i) converting a 6-halo-1,1-dialkoxyhexane compound (6) into a 6,6-dialkoxyhexyl nucleophile (7), (ii) subjecting the 6,6-dialkoxyhexyl nucleophile (7) to a propylene oxide (8) or 1,2-butylene oxide (10) to produce a dialkoxyalkanol compound (9), (iii) subsequently subjecting the dialkoxyalkanol compound (9) to an acylation reaction to produce a dialkoxyacyloxyalkane compound (5), and (iv) subsequently hydrolyzing the dialkoxyacyloxyalkane compound (5).

[0026] (i) The above 6,6-dialkoxyhexyl nucleophile (7) and its preparation method (a) The 6,6-dialkoxyhexyl nucleophile (7) is described below. The 6,6-dialkoxyhexyl nucleophilic reagent (7) is represented by the following general formula (7). [ka]

[0027] In the above general formula (7), M 2 Li, MgZ 2 , CuZ 2 Or CuLiZ 2 where Z 2 represents a halogen atom or a 6,6-dialkoxyhexyl group. 2 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 (7), R 3 and R 4 are each independently a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably a monovalent hydrocarbon group having 1 to 10 carbon atoms, more preferably a monovalent hydrocarbon group having 1 to 5 carbon atoms, and even more preferably a monovalent hydrocarbon group having 1 to 4 carbon atoms, or R 3 and R 4are bonded together R 3 -R 4 represents a divalent hydrocarbon group having 2 to 10 carbon atoms, preferably 2 to 5 carbon atoms. Examples of the monovalent hydrocarbon group 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, and may be hydrocarbon groups that are isomers of these. In addition, some of the hydrogen atoms of these hydrocarbon groups may be substituted with methyl or ethyl groups. From the viewpoint of handling, preferred monovalent hydrocarbon groups are a methyl group, an ethyl group, an n-propyl group, and an n-butyl group. R 3 and R 4 are bonded together R 3 -R 4 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 groups; 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 groups; linear unsaturated hydrocarbon groups such as 1-vinylethylene groups; branched unsaturated hydrocarbon groups such as 2-methylene-1,3-propylene groups; cyclic hydrocarbon groups such as 1,2-cyclopropylene and 1,2-cyclobutylene groups, and the like, and may also be hydrocarbon groups that are isomers of these. In addition, some of the hydrogen atoms of these hydrocarbon groups may be substituted with methyl or ethyl groups. In consideration of the 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. Taking these into consideration, 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. In the above general formula (7), M 2 MgZ 2 When the 6,6-dialkoxyhexyl nucleophile (7:M 2 =MgZ 2 ) is a Grignard reagent.

[0028] Specific examples of 6,6-dialkoxyhexyl nucleophiles (7) include the following compounds: 6,6-dialkoxyhexyllithium compounds (M) such as 6,6-dimethoxyhexyllithium, 6,6-diethoxyhexyllithium, 6,6-dipropyloxyhexyllithium, 6,6-dibutyloxyhexyllithium, 6,6-dipentyloxyhexyllithium, 6,6-dihexyloxyhexyllithium, 6,6-diheptyloxyhexyllithium, 6,6-dioctyloxyhexyllithium, 6,6-dinonyloxyhexyllithium, 6,6-didecyloxyhexyllithium, [5-(1,3-dioxolan-2-yl)pentyl]lithium, and [5-(1,3-dioxan-2-yl)pentyl]lithium. 2 =Li); 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 hexylmagnesium chloride, 6,6-didecyloxyhexylmagnesium chloride, [5-(1,3-dioxolan-2-yl)pentyl]magnesium chloride, [5-(1,3-dioxan-2-yl)pentyl]magnesium chloride, 6,6-dimethoxyhexylmagnesium bromide, 6,6-diethoxyhexylmagnesium bromide, 6,6-dipropyloxyhexylmagnesium bromide, 6,6-dibutyloxyhexylmagnesium bromide, 6,6-dipentyloxyhexylmagnesium bromide, 6,6-di Hexyloxyhexylmagnesium bromide, 6,6-diheptyloxyhexylmagnesium bromide, 6,6-dioctyloxyhexylmagnesium bromide, 6,6-dinonyloxyhexylmagnesium bromide, 6,6-didecyloxyhexylmagnesium bromide, [5-(1,3-dioxolan-2-yl)pentyl]magnesium bromide, [5-(1,3-dioxan-2-yl)pentyl]magnesium bromide, 6,6-dimethoxyhexylmagnesium iodide, 6,6-diethoxyhexylmagnesium bromide xyl magnesium iodide, 6,6-dipropyloxyhexyl magnesium iodide, 6,6-dibutyloxyhexyl magnesium iodide, 6,6-dipentyloxyhexyl magnesium iodide, 6,6-dihexyloxyhexyl magnesium iodide, 6,6-diheptyloxyhexyl magnesium iodide, 6,6-dioctyloxyhexyl magnesium iodide, 6,6-dinonyloxyhexyl magnesium iodide, 6,6-didecyloxyhexyl magnesium iodide, [5-(1,6,6-dialkoxyhexylmagnesium halide compounds such as [3-dioxolan-2-yl)pentyl]magnesium iodide and [5-(1,3-dioxan-2-yl)pentyl]magnesium iodide (M, 2 =MgZ 2 (The above is a Grignard reagent); Bis[6,6-dialkoxyhexyl]cuprate compounds such as bis[6,6-dimethoxyhexyl]cuprate, bis[6,6-diethoxyhexyl]cuprate, bis[6,6-dipropyloxyhexyl]cuprate, bis[6,6-dibutyloxyhexyl]cuprate, bis[6,6-dipentyloxyhexyl]cuprate, bis[6,6-dihexyloxyhexyl]cuprate, bis[6,6-diheptyloxyhexyl]cuprate, bis[6,6-dioctyloxyhexyl]cuprate, bis[6,6-dinonyloxyhexyl]cuprate and bis[6,6-didecyloxyhexyl]cuprate (M 2 =CuZ 2 ); and Gilman reagents (M) such as lithium bis[6,6-dialkoxyhexyl]cuprate compounds, such as lithium bis[6,6-dimethoxyhexyl]cuprate, lithium bis[6,6-diethoxyhexyl]cuprate, lithium bis[6,6-dipropyloxyhexyl]cuprate, lithium bis[6,6-dibutyloxyhexyl]cuprate, lithium bis[6,6-dipentyloxyhexyl]cuprate, lithium bis[6,6-dihexyloxyhexyl]cuprate, lithium bis[6,6-diheptyloxyhexyl]cuprate, lithium bis[6,6-dioctyloxyhexyl]cuprate, lithium bis[6,6-dinonyloxyhexyl]cuprate and lithium bis[6,6-didecyloxyhexyl]cuprate 2 =CuLiZ 2 (The above are Gilman reagents.) From the viewpoint of reactivity, Grignard reagents such as 6,6-dimethoxyhexylmagnesium halide compounds are preferred.

[0029] (b) Next, a method for producing the above 6,6-dialkoxyhexyl nucleophilic reagent (7) will be described below. The 6,6-dialkoxyhexyl nucleophilic reagent (7) can be prepared using the above 6-halo-1,1-dialkoxyhexane compound (6). The 6-halo-1,1-dialkoxyhexane compound (6) can be prepared, for example, according to the method described in JP 2019-189535 A.

[0030] For example, the 6,6-dialkoxyhexyl nucleophile (7) is 2 MgZ 2 In the case of 6,6-dialkoxyhexylmagnesium halide reagent (7:M 2 =MgZ 2 A method for producing ) (i.e., a Grignard reagent) will be described as an example. 6,6-Dialkoxyhexylmagnesium halide reagent (7:M 2 =MgZ 2 In the case of (a), for example, as shown in the following chemical reaction formula, the above 6-halo-1,1-dialkoxyhexane compound (6) can be prepared by reacting with magnesium in a solvent.

[0031] [ka]

[0032] The amount of magnesium used is preferably 1.0 to 2.0 gram atoms per mole of the 6-halo-1,1-dialkoxyhexane compound (6) from the viewpoint of completing the reaction.

[0033] 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, hydrocarbon solvents such as toluene and xylene are preferred; and ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran are more preferred from the viewpoint of the reaction rate of the production of the Grignard reagent. 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 6-halo-1,1-dialkoxyhexane compound (6) from the viewpoint of reactivity.

[0034] 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.

[0035] (ii) The dialkoxyalkanol compound (9) and its production method (a) The dialkoxyalkanol compound (9) is explained below. The dialkoxyalkanol compound (9) is represented by the following general formula (9). [ka]

[0036] In the above general formula (9), R 3 and R 4is as defined in general formula (7), and n is as defined in general formula (1) above. In this specification, when n is 0, the compound is represented as a dialkoxyalkanol compound (9: n = 0), or a dialkoxyalkanol compound (9A), or a 9,9-dialkoxy-2-nonanol compound (9A), and when n is 1, the compound is represented as a dialkoxyalkanol compound (9: n = 1), or a dialkoxyalkanol compound (9B), or a 10,10-dialkoxy-3-decanol compound (9B).

[0037] Specific examples of the dialkoxyalkanol compound (9), namely, the dialkoxyalkanol compound (9A) and the dialkoxyalkanol compound (9B), are described below. In the case of the dialkoxyalkanol compound (9A), the following compounds can be mentioned: 9,9-dialkoxy-2-nonanol compounds such as 9,9-dimethoxy-2-nonanol, 9,9-diethoxy-2-nonanol, 9,9-dipropyloxy-2-nonanol, 9,9-dibutyloxy-2-nonanol, 9,9-dipentyloxy-2-nonanol, 9,9-dihexyloxy-2-nonanol, 9,9-diheptyloxy-2-nonanol, 9,9-dioctyloxy-2-nonanol, 9,9-dinonyloxy-2-nonanol, 9,9-didecyloxy-2-nonanol, α-methyl-1,3-dioxolane-2-heptanol, and α-methyl-1,3-dioxane-2-heptanol. In the case of the dialkoxyalkanol compound (9B), the following compounds can be mentioned: 10,10-dialkoxy-3-decanol compounds such as 10,10-dimethoxy-3-decanol, 10,10-diethoxy-3-decanol, 10,10-dipropyloxy-3-decanol, 10,10-dibutyloxy-3-decanol, 10,10-dipentyloxy-3-decanol, 10,10-dihexyloxy-3-decanol, 10,10-diheptyloxy-3-decanol, 10,10-dioctyloxy-3-decanol, 10,10-dinonyloxy-3-decanol, 10,10-didecyloxy-3-decanol, α-ethyl-1,3-dioxolane-2-heptanol, and α-ethyl-1,3-dioxane-2-heptanol.

[0038] (b) Next, a method for producing the above dialkoxyalkanol compound (9) will be described below. The dialkoxyalkanol compound (9) can be prepared using the 6,6-dialkoxyhexyl nucleophile (7) described above, as shown in the following reaction scheme.

[0039] [ka]

[0040] The production method includes at least a step of subjecting a 6,6-dialkoxyhexyl nucleophilic reagent (7) to a nucleophilic addition reaction with propylene oxide represented by the above formula (8) or 1,2-butylene oxide represented by the above formula (10) to obtain a dialkoxyalkanol compound (9A) or (9B), respectively.

[0041] In the above nucleophilic addition reaction, the 6,6-dialkoxyhexyl nucleophile (7) may be used alone or in combination, if necessary.

[0042] Propylene oxide (8) and 1,2-butylene oxide (10) may each be commercially available or may be independently synthesized.

[0043] In the nucleophilic addition reaction, the amount of the 6,6-dialkoxyhexyl nucleophilic reagent (7) used is preferably 0.6 to 1.3 moles per mole of the propylene oxide (8) or 1,2-butylene oxide (10) from the viewpoint of economic efficiency.

[0044] 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 , N Examples of polar solvents include '-dimethylpropyleneurea (DMPU), hexamethylphosphoric triamide (HMPA), dichloromethane, chloroform, etc., and from the viewpoint of reactivity, preferred are hydrocarbon solvents such as toluene and xylene; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran; and acetonitrile, 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. 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 6,6-dialkoxyhexyl nucleophilic reagent (7) from the viewpoint of reactivity.

[0045] 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 6,6-dialkoxyhexyl nucleophilic reagent (7) from the viewpoint of reaction rate and / or post-treatment.

[0046] 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 6,6-dialkoxyhexyl nucleophilic reagent (7) from the viewpoint of reactivity.

[0047] 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. 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. When the lithium halide is used, the amount of the lithium halide used is preferably more than 0 and 0.250 mol per mol of the 6,6-dialkoxyhexyl nucleophilic reagent (7) from the viewpoint of reactivity.

[0048] The reaction temperature in the nucleophilic addition reaction varies depending on the 6,6-dialkoxyhexyl nucleophilic reagent (7) 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 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.

[0049] (iii) The dialkoxyacyloxyalkane compound (5) and its production method (a) The dialkoxyacyloxyalkane compound (5) is represented by the following general formula (5). [ka]

[0050] In the above general formula (5), R 3 and R 4 is as defined in the general formula (7), and n and R 1 is as defined in general formula (1). In this specification, when n is 0, it is represented as a 9,9-dialkoxy-2-acyloxynonane compound (5: n = 0) or a 9,9-dialkoxy-2-acyloxynonane compound (5A), and when n is 1, it is represented as a 9,9-dialkoxy-2-acyloxydecane compound (5: n = 1) or a 9,9-dialkoxy-2-acyloxydecane compound (5B).

[0051] Specific examples of the dialkoxyacyloxyalkane compound (5), ie, a 9,9-dialkoxy-2-acyloxynonane compound (5A) and a 9,9-dialkoxy-2-acyloxydecane compound (5B), are described below. In the case of the 9,9-dialkoxy-2-acyloxynonane compound (5A), the following compounds can be mentioned: 9,9-dialkoxy-2-acetyloxynonane compounds such as 9,9-dimethoxy-2-acetyloxynonane, 9,9-diethoxy-2-acetyloxynonane, 9,9-dipropyloxy-2-acetyloxynonane, 9,9-dibutyloxy-2-acetyloxynonane, 9,9-dipentyloxy-2-acetyloxynonane, 9,9-dihexyloxy-2-acetyloxynonane, 9,9-diheptyloxy-2-acetyloxynonane, 9,9-dioctyloxy-2-acetyloxynonane, 9,9-dinonyloxy-2-acetyloxynonane, 9,9-didecyloxy-2-acetyloxynonane, α-methyl-1,3-dioxolane-2-heptyl acetate, and α-methyl-1,3-dioxane-2-heptyl acetate; 9,9-dialkoxy-2-pivaloyloxynonane compounds such as 9,9-dimethoxy-2-pivaloyloxynonane, 9,9-diethoxy-2-pivaloyloxynonane, 9,9-dipropyloxy-2-pivaloyloxynonane, 9,9-dibutyloxy-2-pivaloyloxynonane, 9,9-dipentyloxy-2-pivaloyloxynonane, 9,9-dihexyloxy-2-pivaloyloxynonane, 9,9-diheptyloxy-2-pivaloyloxynonane, 9,9-dioctyloxy-2-pivaloyloxynonane, 9,9-dinonyloxy-2-pivaloyloxynonane and 9,9-didecyloxy-2-pivaloyloxynonane; and 9,9-dialkoxy-2-benzyloxynonane compounds such as 9,9-dimethoxy-2-benzyloxynonane, 9,9-diethoxy-2-benzyloxynonane, 9,9-dipropyloxy-2-benzyloxynonane, 9,9-dibutyloxy-2-benzyloxynonane, 9,9-dipentyloxy-2-benzyloxynonane, 9,9-dihexyloxy-2-benzyloxynonane, 9,9-diheptyloxy-2-benzyloxynonane, 9,9-dioctyloxy-2-benzyloxynonane, 9,9-dinonyloxy-2-benzyloxynonane and 9,9-didecyloxy-2-benzyloxynonane. In the case of the 9,9-dialkoxy-2-acyloxydecane compound (5B), the following compounds can be mentioned: 10,10-dialkoxy-3-acetyloxydecane compounds such as 10,10-dimethoxy-3-acetyloxydecane, 10,10-diethoxy-3-acetyloxydecane, 10,10-dipropyloxy-3-acetyloxydecane, 10,10-dibutyloxy-3-acetyloxydecane, 10,10-dipentyloxy-3-acetyloxydecane, 10,10-dihexyloxy-3-acetyloxydecane, 10,10-diheptyloxy-3-acetyloxydecane, 10,10-dioctyloxy-3-acetyloxydecane, 10,10-dinonyloxy-3-acetyloxydecane, 10,10-didecyloxy-3-acetyloxydecane, α-ethyl-1,3-dioxolane-2-heptyl acetate, and α-ethyl-1,3-dioxane-2-heptyl acetate; 10,10-dialkoxy-3-pivaloyloxydecane compounds such as 10,10-dimethoxy-3-pivaloyloxydecane, 10,10-diethoxy-3-pivaloyloxydecane, 10,10-dipropyloxy-3-pivaloyloxydecane, 10,10-dibutyloxy-3-pivaloyloxydecane, 10,10-dipentyloxy-3-pivaloyloxydecane, 10,10-dihexyloxy-3-pivaloyloxydecane, 10,10-diheptyloxy-3-pivaloyloxydecane, 10,10-dioctyloxy-3-pivaloyloxydecane, 10,10-dinonyloxy-3-pivaloyloxydecane and 10,10-didecyloxy-3-pivaloyloxydecane; and 10,10-dialkoxy-3-benzyloxydecane compounds such as 10,10-dimethoxy-3-benzyloxydecane, 10,10-diethoxy-3-benzyloxydecane, 10,10-dipropyloxy-3-benzyloxydecane, 10,10-dibutyloxy-3-benzyloxydecane, 10,10-dipentyloxy-3-benzyloxydecane, 10,10-dihexyloxy-3-benzyloxydecane, 10,10-diheptyloxy-3-benzyloxydecane, 10,10-dioctyloxy-3-benzyloxydecane, 10,10-dinonyloxy-3-benzyloxydecane, and 10,10-didecyloxy-3-benzyloxydecane. (b) Next, a method for producing the above dialkoxyacyloxyalkane compound (5) will be described below. The dialkoxyacyloxyalkane compound (5) can be prepared, for example, by using the dialkoxyalkanol compound (9) as shown in the following chemical reaction formula.

[0052] [ka]

[0053] In the above general formula (5), R 3 and R 4 is as defined in the general formula (7), and n and R 1 is as defined in general formula (1).

[0054] The production method includes a step of subjecting dialkoxyalkanol compound (9) to an acylation reaction.

[0055] The acylation reaction can be carried out, for example, by a method in which the hydroxyl group of the dialkoxyalkanol compound (9) is acylated using an acylating agent. The acylating agents include the following compounds: Carboxylic acids such as acetic acid, propanoic acid, butanoic acid, pivalic acid and benzoic acid; Acid anhydrides such as acetic anhydride, pivalic anhydride and benzoic anhydride; acyl halide compounds such as acetyl chloride, acetyl bromide, acetyl iodide, propanoyl chloride, propanoyl bromide, propanoyl iodide, butyryl chloride, butyryl bromide, butyryl iodide, pivaloyl chloride, pivaloyl bromide, pivaloyl iodide, benzoyl chloride, benzoyl bromide and benzoyl iodide; Alkanoic acid ester compounds such as methyl acetate, ethyl acetate, methyl propanoate, ethyl propanoate, methyl butanoate, ethyl butanoate, methyl pivalate and ethyl pivalate; and Benzoic acid ester compounds such as methyl benzoate and ethyl benzoate. As the acylating agent, from the viewpoint of reactivity, acid anhydrides and acyl halide compounds are preferred, and acid anhydrides are more preferred. The amount of the acylating agent used is preferably 1.0 to 10.0 mol, more preferably 1.0 to 5.0 mol, per mol of the dialkoxyalkanol compound (9) from the viewpoints of reactivity and / or economic efficiency.

[0056] For the acylation, an acid or a base may be used, if necessary. Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid, and nitric acid; aromatic sulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid; and Lewis acids such as aluminum trichloride, aluminum ethoxide, aluminum isopropoxide, aluminum oxide, boron trifluoride, boron trichloride, boron tribromide, magnesium chloride, magnesium bromide, magnesium iodide, zinc chloride, zinc bromide, zinc iodide, tin tetrachloride, tin tetrabromide, dibutyltin dichloride, dibutyltin dimethoxide, dibutyltin oxide, titanium tetrachloride, titanium tetrabromide, titanium(IV) methoxide, titanium(IV) ethoxide, titanium(IV) isopropoxide, and titanium(IV) oxide. The acid may be used alone or in combination of two or more kinds, if necessary. When the acid is used, the amount of the acid used is preferably more than 0 to 3.00 mol, more preferably more than 0 to 1.50 mol, per mol of the dialkoxyalkanol compound (9) from the viewpoints of reactivity and / or economic efficiency.

[0057] The base includes the following compounds: Trimethylamine, triethylamine and N , N - Trialkylamine compounds such as diisopropylethylamine; Cyclic amine compounds such as piperidine, pyrrolidine and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); Pyridine, lutidine, N , N -dimethylaniline, N , N -diethylaniline, N , N - aromatic amine compounds such as dibutylaniline and 4-dimethylaminopyridine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide, sodium t-amyloxide, lithium methoxide, lithium ethoxide, lithium t-butoxide, lithium t-amyloxide, potassium methoxide, potassium ethoxide, potassium t-butoxide, and potassium t-amyloxide; Alkyllithium such as methyllithium, ethyllithium, propyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, pentyllithium, hexyllithium, heptyllithium, octyllithium, nonyllithium and decyllithium; Grignard reagents such as methylmagnesium chloride, methylmagnesium bromide and methylmagnesium iodide, ethylmagnesium chloride, ethylmagnesium bromide and ethylmagnesium iodide, propylmagnesium chloride, propylmagnesium bromide and propylmagnesium iodide, butylmagnesium chloride, butylmagnesium bromide and butylmagnesium iodide, pentylmagnesium chloride, pentylmagnesium bromide and pentylmagnesium iodide, hexylmagnesium chloride, hexylmagnesium bromide and hexylmagnesium iodide, heptylmagnesium chloride, heptylmagnesium bromide and heptylmagnesium iodide, octylmagnesium chloride, octylmagnesium bromide and octylmagnesium iodide, nonylmagnesium chloride, nonylmagnesium bromide and nonylmagnesium iodide, decylmagnesium chloride, decylmagnesium bromide and decylmagnesium iodide; and Metal acetylides such as lithium acetylide, sodium acetylide, potassium acetylide, calcium acetylide and silver acetylide. The base may be used alone or in combination of two or more types, if necessary. When the base is used, the amount of the base used is preferably more than 0 to 10.0 mol, more preferably more than 0 to 5.0 mol, per mol of the dialkoxyalkanol compound (9) from the viewpoints of reactivity and / or economic efficiency.

[0058] The acylation 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; 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, dichloromethane, chloroform, and hexamethylphosphoric triamide (HMPA). From the viewpoint of reactivity, preferred are ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran; and hydrocarbon solvents such as 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 acylation may be carried out in the presence of a solvent, if necessary, but the reaction may also be carried out without a solvent. The amount of the solvent used in the acylation is preferably more than 0 to 5000 g, and more preferably more than 0 to 2000 g, per mol of the dialkoxyalkanol compound (9) from the viewpoint of reactivity.

[0059] The reaction temperature in the acylation varies depending on the acylating agent and / or solvent used, but is preferably −40 to 120° C., more preferably −20 to 100° C., and even more preferably 0 to 80° C., from the viewpoint of reactivity. The reaction time for the acylation is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0060] In addition, the dialkoxyalkanol compound (9) and the dialkoxyacyloxyalkane compound (5) may be produced by separately carrying out a nucleophilic substitution reaction and an acylation reaction, respectively, or by carrying out the nucleophilic substitution reaction and then the acylation reaction (see Examples 3 and 4 below). By carrying out the reactions successively, it is possible to reduce the amount of solvent and / or shorten the reaction time, which is more preferable.

[0061] (iv) The above 8-(acyloxy)alkanal compound (1) and its production method (a) The 8-(acyloxy)alkanal compound (1) is as described above. (b) Next, a method for producing the 8-(acyloxy)alkanal compound (1) will be described below. The 8-(acyloxy)alkanal compound (1) can be prepared using the dialkoxyacyloxyalkane compound (5) as shown in the following chemical reaction scheme.

[0062] [ka]

[0063] The method for producing the 8-(acyloxy)alkanal compound (1) comprises the step of subjecting a dialkoxyacyloxyalkane compound (5) to a hydrolysis reaction.

[0064] In the above hydrolysis reaction, the dialkoxyacyloxyalkane compound (5) may be used alone or in combination with two or more kinds, if necessary.

[0065] The hydrolysis reaction can be carried out, for example, using an acid and water. The acid may be an inorganic acid such as hydrochloric acid or hydrobromic acid; p toluenesulfonic acid, benzenesulfonic acid, trifluoroacetic acid, acetic acid, formic acid, oxalic acid, iodotrimethylsilane, titanium tetrachloride, etc., and from the viewpoint of reactivity, acetic acid, formic acid and oxalic acid, p Toluenesulfonic acid and benzenesulfonic acid are preferred, from the viewpoint of reaction yield. p Toluenesulfonic acid and benzenesulfonic acid are more 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 0.01 to 10.0 mol per 1 mol of the dialkoxyacyloxyalkane compound (5). The amount of water used is preferably 18 to 7000 g, more preferably 18 to 3000 g, per mol of the dialkoxyacyloxyalkane compound (5) from the viewpoint of reactivity.

[0066] In the hydrolysis reaction, a solvent may be further used, if necessary, in addition to the above-mentioned acid or water. 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 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. In addition, commercially available solvents may 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 preferable from the viewpoint of reactivity. p When toluenesulfonic acid or benzenesulfonic acid is used, preferred are hydrocarbon solvents such as toluene and xylene; and alcohol solvents such as methanol and ethanol. The amount of the solvent used is preferably more than 0 to 7000 g, more preferably more than 0 to 3000 g, per mol of the dialkoxyacyloxyalkane compound (5) from the viewpoint of reactivity.

[0067] 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 in 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 from the viewpoint of reactivity.

[0068] In the manner described above, it is possible to produce 8-(acyloxy)alkanal compound (1), which is a synthetic intermediate useful for producing 2,9-diacetoxyundecane represented by the following general formula (4). [ka]

[0069] Incidentally, initially, as a production intermediate of the 2,9-diacetoxyundecane (4), it was considered to utilize an 8-hydroxyalkanal compound (see formula (11) described in Comparative Example 1 below) in which the hydroxyl group of the 8-(acyloxy)alkanal compound (1) is not protected with an acyl group, rather than the above 8-(acyloxy)alkanal compound (1). This was because it was thought to be wasteful to once protect the hydroxyl group with an acyl group and then deprotect it again to obtain a free hydroxyl group. However, it became clear that when synthesizing the 8-hydroxyalkanal compound (11), the hydroxyl group reacts with the formyl group, resulting in a significant decrease in yield (see Comparative Example 1 below). Therefore, as a result of the investigation, it became clear that, although it may seem like a roundabout way at first glance, it is extremely important from the viewpoint of yield to obtain an aldehyde by hydrolyzing the acetal in a state in which the hydroxyl group is protected.

[0070] III. Production method of 2,9-diacetoxyundecane 2,9-Diacetoxyundecane (4), which is one of the target compounds of the present invention, can be prepared, for example, by using the above 8-(acyloxy)alkanal compound (1) as shown in the following chemical reaction scheme.

[0071] [ka]

[0072] That is, 2,9-diacetoxyundecane (4) can be produced by (i) subjecting 8-(acyloxy)alkanal compound (1) to a nucleophilic addition reaction with an alkyl nucleophile (2) to carry out nucleophilic addition to the formyl group and deprotection of the acyl group to produce 2,9-undecanediol (3), and (ii) subsequently acetylating the 2,9-undecanediol (3).

[0073] (i) Regarding the method for producing the above 2,9-undecanediol (3) (a) The method for producing the 2,9-undecanediol (3) is described below. The 2,9-undecanediol (3) can be prepared using the above 8-(acyloxy)alkanal compound (1) as shown in the following chemical reaction scheme.

[0074] [ka]

[0075] The production method includes a step of subjecting an 8-(acyloxy)alkanal compound (1) to a nucleophilic addition reaction with an alkyl nucleophile represented by the above general formula (2).

[0076] The alkyl nucleophile (2) is described below. In the general formula (2), M 1 Li, MgZ 1 , CuZ 1 Or CuLiZ 1 where Z 1represents a halogen atom, a methyl group or an ethyl group, and n is as defined in general formula (1) above.

[0077] Specific examples of alkyl nucleophiles (2) include the following compounds: Alkyl lithium compounds such as methyllithium and ethyllithium (M 1 =Li); Alkyl magnesium halide compounds such as methyl magnesium chloride, methyl magnesium bromide, methyl magnesium iodide, ethyl magnesium chloride, ethyl magnesium bromide and ethyl magnesium iodide (M 1 =MgZ 1 (The above is a Grignard reagent); Dialkylcuprate compounds such as dimethylcuprate and diethylcuprate (M 1 =CuZ 1 ); and Gilman's reagents (M) such as lithium dialkylcuprate compounds, e.g., lithium dimethylcuprate and lithium diethylcuprate 1 =CuLiZ 1 (The above are Gilman reagents.)

[0078] In the above nucleophilic addition reaction, the alkyl nucleophile (2) may be used alone or in combination of two or more kinds, if necessary.

[0079] In the nucleophilic addition reaction, the amount of the alkyl nucleophilic reagent (2) used is preferably 3.0 to 15.0 mol, more preferably 3.0 to 10.0 mol, and even more preferably 3.1 to 6.0 mol, per 1 mol of the 8-(acyloxy)alkanal compound (1) from the viewpoint of reactivity.

[0080] 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; 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, etc., and from the viewpoint of reactivity, preferred are hydrocarbon solvents such as toluene and xylene; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran; and acetonitrile, 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. 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 1 mol of the 8-(acyloxy)alkanal compound (1) from the viewpoint of reactivity.

[0081] The reaction temperature in the nucleophilic addition reaction varies depending on the 8-(acyloxy)alkanal compound (1) used, but is preferably −78 to 150° C., more preferably −20 to 100° C., and even more preferably 20 to 70° C., from the viewpoint of reactivity. 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.

[0082] (ii) Regarding the method for producing the above 2,9-diacetoxyundecane (4) (a) A method for producing 2,9-diacetoxyundecane (4) is described below. The 2,9-diacetoxyundecane (4) can be prepared using the above 2,9-undecanediol (3).

[0083] [ka]

[0084] The production method includes a step of subjecting 2,9-undecanediol (3) to an acetylation reaction. The acetylation reaction can be carried out, for example, by a method in which the hydroxyl groups of 2,9-undecanediol (3) are acetylated using an acetylating agent. The acetylating agents include the following compounds: Acetic acid; Acid anhydrides such as acetic anhydride; Acetyl halide compounds such as acetyl chloride, acetyl bromide and acetyl iodide; Acetate compounds such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, pentyl acetate and hexyl acetate; As the acetylating agent, from the viewpoint of reactivity, acid anhydrides and acetyl halide compounds are preferred, and acid anhydrides are more preferred. The amount of the acylating agent used is preferably 2.0 to 15.0 mol, more preferably 2.0 to 10.0 mol, and even more preferably 2.1 to 8.0 mol, per mol of 2,9-undecanediol (3), from the viewpoints of reactivity and / or economy.

[0085] The acetylation may be carried out using an acid or a base, if necessary.

[0086] Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid, and nitric acid; aromatic sulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid; and Lewis acids such as aluminum trichloride, aluminum ethoxide, aluminum isopropoxide, aluminum oxide, boron trifluoride, boron trichloride, boron tribromide, magnesium chloride, magnesium bromide, magnesium iodide, zinc chloride, zinc bromide, zinc iodide, tin tetrachloride, tin tetrabromide, dibutyltin dichloride, dibutyltin dimethoxide, dibutyltin oxide, titanium tetrachloride, titanium tetrabromide, titanium(IV) methoxide, titanium(IV) ethoxide, titanium(IV) isopropoxide, and titanium(IV) oxide. The acid may be used alone or in combination of two or more kinds, if necessary. When the acid is used, the amount of the acid used is preferably more than 0 to 3.00 mol, more preferably more than 0 to 1.50 mol, per mol of 2,9-undecanediol (3) from the viewpoints of reactivity and / or economic efficiency.

[0087] The base includes the following compounds: Trimethylamine, triethylamine and N , N - Trialkylamine compounds such as diisopropylethylamine; Cyclic amine compounds such as piperidine, pyrrolidine and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); Pyridine, lutidine, N , N -dimethylaniline, N , N -diethylaniline, N , N - Aromatic amine compounds such as dibutylaniline and 4-dimethylaminopyridine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide, sodium t-amyloxide, lithium methoxide, lithium ethoxide, lithium t-butoxide, lithium t-amyloxide, potassium methoxide, potassium ethoxide, potassium t-butoxide, and potassium t-amyloxide; Alkyllithium such as methyllithium, ethyllithium, propyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, pentyllithium, hexyllithium, heptyllithium, octyllithium, nonyllithium and decyllithium; Grignard reagents such as methylmagnesium chloride, methylmagnesium bromide and methylmagnesium iodide, ethylmagnesium chloride, ethylmagnesium bromide and ethylmagnesium iodide, propylmagnesium chloride, propylmagnesium bromide and propylmagnesium iodide, butylmagnesium chloride, butylmagnesium bromide and butylmagnesium iodide, pentylmagnesium chloride, pentylmagnesium bromide and pentylmagnesium iodide, hexylmagnesium chloride, hexylmagnesium bromide and hexylmagnesium iodide, heptylmagnesium chloride, heptylmagnesium bromide and heptylmagnesium iodide, octylmagnesium chloride, octylmagnesium bromide and octylmagnesium iodide, nonylmagnesium chloride, nonylmagnesium bromide and nonylmagnesium iodide, decylmagnesium chloride, decylmagnesium bromide and decylmagnesium iodide; Metal acetylides, such as lithium acetylide, sodium acetylide, potassium acetylide, calcium acetylide, and silver acetylide; and Inorganic metal salts such as potassium carbonate, sodium carbonate and calcium carbonate. The base may be used alone or in combination of two or more types, if necessary. When the base is used, the amount of the base used is preferably more than 0 to 10.0 mol, more preferably more than 0 to 5.0 mol, per mol of the dialkoxyalkanol compound (9) from the viewpoints of reactivity and / or economic efficiency.

[0088] The acetylation may be carried out using a common solvent, for example, a solvent as required. 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, acetonitrile, dichloromethane, chloroform, and hexamethylphosphoric triamide (HMPA). From the viewpoint of reactivity, preferred are ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran; and hydrocarbon solvents such as 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 acetylation may be carried out in the presence of a solvent, if necessary, but the reaction may also be carried out without a solvent. The amount of the solvent used in the acetylation is preferably more than 0 to 5000 g, and more preferably more than 0 to 2000 g, per 1 mol of the 2,9-undecanediol (3) from the viewpoint of reactivity.

[0089] The reaction temperature in the acetylation varies depending on the acylating agent and / or solvent used, but is preferably −40 to 100° C., more preferably −20 to 80° C., and even more preferably 0 to 80° C., from the viewpoint of reactivity. The reaction time for the acetylation is preferably 0.5 to 100 hours from the viewpoint of reactivity.

[0090] In addition, in the production of 2,9-undecanediol (3) and 2,9-diacetoxyundecane (4), the nucleophilic substitution reaction and the acetylation reaction may be carried out separately, or the nucleophilic substitution reaction may be followed by the acetylation reaction (see Examples 7 and 8 below). By carrying out the reactions successively, it is possible to reduce the amount of solvent and / or the reaction time, and also to avoid contact of the water-soluble 2,9-undecanediol (3) with water, thereby increasing the two-step yield of 2,9-diacetoxyundecane (4).

[0091] As described above, according to the present invention, the synthetic intermediate 8-(acyloxy)alkanal compound (1) can be simply and efficiently produced. In addition, according to the present invention, the Swedish midge (scientific name: Contarinia buttons The present invention can efficiently produce 2,9-diacetoxyundecane (4), which is the sex pheromone of the genus Pseudomonas spp., in a short number of steps with high productivity. In other words, by continuously carrying out the acylation and acetylation steps, 2,9-diacetoxyundecane (4) can be produced in a good yield from 6-halo-1,1-dialkoxyhexane compound (6) in four steps.

[0092] [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.

[0093] 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 is tetrahydrofuran, Ph is a phenyl group, Ts is a toluenesulfonyl group, Ac is an acetyl group, and Bu is an n-butyl group. t Bu is third -Butyl and Et represent an ethyl group.

[0094] [Example 1] 9,9-diethoxy-2-nonanol (9A:R 3 =R 4 =Et)

[0095] [ka]

[0096] Magnesium (89.30 g, 3.68 gram atoms) and tetrahydrofuran (1050.00 g) were added to the reactor at room temperature and stirred at 60-65° C. for 42 minutes. Next, 6-chloro-1,1-diethoxyhexane (6:R 3 =R 4 X=Et, X=Cl) (744.93 g, 3.50 mol, purity 98.08%) 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 3 hours to obtain 6,6-diethoxyhexylmagnesium chloride (7:R 3 =R4 = Et, M 2 = MgCl) was prepared.

[0097] The internal temperature of the reactor was then cooled to 0-10°C, followed by adding cuprous chloride (0.73g, 0.0070mol) to the reactor, and then adding propylene oxide (233.77g, 4.02mol) dropwise at 5-30°C. After the dropwise addition was completed, the mixture was stirred at 15-25°C for 2.5 hours. Next, an aqueous acetic acid solution (acetic acid (477.65g) and water (964.31g)) was 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 9,9-diethoxy-2-nonanol (9A:R 3 =R 4 =Et) (727.52 g, 3.06 mol, purity 97.70%, bp = 132.0-141.0 °C / 0.041 kPa (0.31 mmHg)) was obtained in a yield of 87.39%.

[0098] The 9,9-diethoxy-2-nonanol (9A:R 3 =R 4 The spectral data for (Et) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=1.12-1.23(9H,m),1.23-1.62(13H,m),3.43-3.52(2 H,m),3.56-3.65(2H,m).3.54(1H,dt,J=7.2Hz,7.2Hz),4.45(1H,t,J=5.8Hz); 13 C-NMR (125MHz, CDCl3): δ=15.30,18.36,23.43,24.63,25.63,29.38,33.52,39.27,60.78,68.03,102.89 [Mass spectrum] EI-mass spectrum (70 eV): m / z 231 (M + -1), 215, 187, 169, 141, 123, 103, 75, 47, 29 [Infrared absorption spectrum] (D-ATR): ν=3421, 2974, 2930, 2858, 1457, 1374, 1345, 1126, 1062, 996, 944cm -1

[0099] [Example 2] 10,10-diethoxy-3-decanol (9B:R 3 =R 4 =Et)

[0100] [ka]

[0101] Magnesium (89.30 g, 3.68 gram atoms) and tetrahydrofuran (1050.00 g) were added to the reactor at room temperature and stirred at 60-65° C. for 37 minutes. Next, 6-chloro-1,1-diethoxyhexane (6:R 3 =R 4 X=Et, X=Cl) (744.93 g, 3.50 mol, purity 98.08%) 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 3 hours to obtain 6,6-diethoxyhexylmagnesium chloride (7:R 3 =R 4 = Et, M 2 = MgCl) was prepared.

[0102] The internal temperature of the reactor was then cooled to 0-10°C, followed by adding cuprous chloride (0.73g, 0.0070mol) to the reactor, and then adding 1,2-butylene oxide (290.24g, 4.02mol) dropwise at 5-30°C. After the dropwise addition was completed, the mixture was stirred at 15-25°C for 2.5 hours. Next, an aqueous acetic acid solution (acetic acid (477.65g) and water (964.31g)) was 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 10,10-diethoxy-3-decanol (9B:R 3 =R 4 =Et) (767.62 g, 3.06 mol, purity 98.21%, bp = 140.0-145.6 °C / 0.17 kPa (1.3 mmHg)) was obtained in a yield of 87.42%.

[0103] The 10,10-diethoxy-3-decanol (9B:R 3=R 4 The spectral data for (Et) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.92(3H,t,J=7.2Hz),1.18(6H,t,J=7.2Hz),1.22(1H,t,J=7.2Hz),1.25-1. 62(14H,m),3.42-3.53(2H,m),3.58-3.65(2H,m),3.69(1H,dt,J=6.9Hz,6.9Hz),4.45(1H,t,J=5.8Hz); 13 C-NMR (125MHz, CDCl3): δ=9.09,9.82,15.31,24.65,25.52,29.40,29.58,30.10,33.53,36.86,60.78,102.89 [Mass spectrum] EI-mass spectrum (70 eV): m / z 245 (M + -1), 229, 201, 183, 171, 155, 137, 103, 75, 47, 29 [Infrared absorption spectrum] (D-ATR): ν=3430, 2974, 2930, 2858, 1462, 1374, 1344, 1126, 1061, 999 cm -1

[0104] [Example 3] 9,9-diethoxy-2-acetyloxynonane (5A:R 3 =R 4 =Et,R 1 =CH3)

[0105] [ka]

[0106] Magnesium (89.30 g, 3.68 gram atoms) and tetrahydrofuran (1050.00 g) were added to the reactor at room temperature and stirred for 20 minutes at 60-65° C. Next, 6-chloro-1,1-diethoxyhexane (6:R 3 =R 4X=Et, X=Cl) (744.93 g, 3.50 mol, purity 98.08%) 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 3 hours to obtain 6,6-diethoxyhexylmagnesium chloride (7:R 3 =R 4 = Et, M 2 = MgCl) was prepared.

[0107] The internal temperature of the reactor was then cooled to 0-10°C, followed by adding cuprous chloride (0.73g, 0.0070mol) to the reactor, and then adding propylene oxide (233.77g, 4.02mol) dropwise at 5-30°C. After the dropwise addition was completed, the mixture was stirred at 15-25°C for 2 hours. Next, acetic anhydride (410.91g, 4.02mol) was added dropwise to the reaction liquid at 20-60°C, and the mixture was stirred at 30-40°C for 1.5 hours. Next, water (964.31g) was added and the mixture was separated, and the obtained organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 9,9-diethoxy-2-acetyloxynonane (5A:R 3 =R 4 =Et,R 1 =CH3) (874.02 g, 3.11 mol, purity 97.67%, bp = 140.0-147.9 °C / 0.44 kPa (3.3 mmHg)) was obtained in a yield of 88.89%.

[0108] The 9,9-diethoxy-2-acetyloxynonane (5A:R 3 =R 4 =Et,R 1 The spectral data for 3H2O(CH3) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=1.16-1.20(9H,m),1.22-1.36(8H,m),1.39-1.61(4H,m),2.00(3H,s ),3.43-3.50(2H,m),3.58-3.65(2H,m),4.45(1H,t,J=5.7Hz),4.86(1H,tq,J=6.1Hz,6.1Hz); 13C-NMR (125MHz, CDCl3): δ=15.31,19.90,21.33,24.61,25.26,29.31,33.51,35.84,60.78,70.96,102.87,170.72 [Mass spectrum] EI-mass spectrum (70 eV): m / z 273 (M + -1), 229, 215, 185, 169, 123, 103, 75, 57, 43, 29 [Infrared absorption spectrum] (D-ATR): ν=2975, 2933, 1860, 1738, 1445, 1373, 1347, 1244, 1127, 1062, 953cm -1

[0109] [Example 4] 10,10-diethoxy-3-acetyloxydecane (5B:R 3 =R 4 =Et,R 1 =CH3)

[0110] [ka]

[0111] Magnesium (89.30 g, 3.68 gram atoms) and tetrahydrofuran (1050.00 g) were added to the reactor at room temperature and stirred for 20 minutes at 60-65° C. Next, 6-chloro-1,1-diethoxyhexane (6:R 3 =R 4 X=Et, X=Cl) (744.93 g, 3.50 mol, purity 98.08%) 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 3 hours to obtain 6,6-diethoxyhexylmagnesium chloride (7:R 3 =R 4 = Et, M 2 = MgCl) was prepared.

[0112] The internal temperature of the reactor was then cooled to 0-10°C, followed by adding cuprous chloride (0.73g, 0.0070mol) to the reactor, and then adding 1,2-butylene oxide (290.24g, 4.02mol) dropwise at 5-30°C. After the dropwise addition was completed, the mixture was stirred at 15-25°C for 2 hours. Next, acetic anhydride (410.91g, 4.02mol) was added dropwise to the reaction liquid at 20-60°C, and the mixture was stirred at 30-40°C for 1.5 hours. Next, water (964.31g) was added and the mixture was separated, and the obtained organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 10,10-diethoxy-3-acetyloxydecane (5B:R 3 =R 4 =Et,R 1 =CH3) (897.83, 3.03 mol, purity 97.24%, bp = 143.0-148.1 °C / 0.059 kPa (0.44 mmHg)) was obtained in a yield of 86.50%.

[0113] The 10,10-diethoxy-3-acetyloxydecane (5B:R 3 =R 4 =Et,R 1 The spectral data for 3H2O(CH3) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.86(3H,t,J=7.3Hz),1.18(6H,t,J=7.3Hz),1.21-1.37(8H,m),1.45-1.62(6H,m ),2.02(3H,s),3.43-3.51(2H,m),3.58-3.66(2H,m),4.45(1H,t,J=5.7Hz),4.78(1H,tt,J=6.3Hz,6.3Hz); 13 C-NMR (125MHz, CDCl3): δ=9.53,15.31,21.20,24.62,25.19,26.89,29.32,29.41,33.51,60.78,75.45,102.88,170.91 [Mass spectrum] EI-mass spectrum (70 eV): m / z 287 (M + -1), 243, 229, 199, 183, 137, 103, 75, 57, 43, 29 [Infrared absorption spectrum] (D-ATR): ν=2973, 2933, 2860, 1738, 1461, 1373, 1243, 1127, 1063, 1019, 955cm -1

[0114] [Example 5] 8-(Acetyloxy)nonanal (1:R 1 =CH3, n=0)

[0115] [ka]

[0116] At room temperature, the reactor was charged with 9,9-diethoxy-2-acetyloxynonane (5A:R 3 =R 4 =Et,R 1 =CH3) (103.58, 0.37 mol, 97.67% purity), p Toluenesulfonic acid monohydrate (0.50 g, 0.0026 mol), water (66.40 g, 3.69 mol), and toluene (40.00 g) were added, and ethanol was distilled off at 60 to 70° C. The reaction rate was confirmed to be 99% or more by GC, and the mixture was subsequently cooled to 20 to 30° C., separated, and the aqueous layer was removed to obtain an organic layer. The obtained organic layer was then distilled under reduced pressure to obtain 8-(acetyloxy)nonanal (1:R 1 =CH3, n = 0) (67.51 g, 0.33 mol, purity 98.85%, bp = 110.0-118.1 °C / 0.19 kPa (1.4 mmHg)) was obtained in a yield of 90.38%.

[0117] The 8-(acetyloxy)nonanal (1:R 1 The spectral data for (=CH3, n=0) is shown below. [Nuclear Magnetic Resonance Spectrum] 1H-NMR (500MHz, CDCl3): δ=1.17(3H,d,J=6.5Hz),1.22-1.35(6H,m),1.40-1.49(1H,m),1.50-1.65(3H ,m),2.01(3H,s),2.40(2H,dt,J=1.9Hz,7.3Hz),4.86(1H,tq,J=6.5Hz,6.5Hz),9.74(1H,t,J=1.9Hz); 13 C-NMR (125MHz, CDCl3): δ=19.89,21.32,21.90,25.11,28.96,29.09,35.75,43.79,70.84,170.72,202.70 [Mass spectrum] EI-mass spectrum (70 eV): m / z 201 (M + +1), 157, 140, 122, 112, 97, 81, 67, 55, 43, 29 [Infrared absorption spectrum] (D-ATR): ν=2977, 2934, 2859, 2719, 1732, 1462, 1373, 1245, 1137, 1022, 952cm -1

[0118] [Example 6] 8-(Acetyloxy)decanal (1:R 1 =CH3, n=1)

[0119] [ka]

[0120] At room temperature, the reactor was charged with 10,10-diethoxy-3-acetyloxydecane (5B:R 3 =R 4 =Et,R 1 =CH3) (109.36 g, 0.37 mol, 97.24% purity); pToluenesulfonic acid monohydrate (0.50 g, 0.0026 mol), water (66.40 g, 3.69 mol), and toluene (40.00 g) were added, and ethanol was distilled off at 60 to 70° C. The reaction rate was confirmed to be 99% or more by GC, and the mixture was subsequently cooled to 20 to 30° C., separated, and the aqueous layer was removed to obtain an organic layer. The obtained organic layer was then distilled under reduced pressure to obtain 8-(acetyloxy)decanal (1:R 1 =CH3, n = 1) (67.45 g, 0.31 mol, purity 98.11%, bp = 110.0-119.1 °C / 0.19 kPa (1.4 mmHg)) was obtained in a yield of 83.75%.

[0121] The 8-(acetyloxy)decanal (1:R 1 The spectral data for (=CH3, n=1) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.85(3H,t,J=7.3Hz),1.20-1.35(6H,m),1.45-1.66(6H,m),2.02( 3H,s),2.40(2H,dt,J=1.9Hz,7.3Hz),4.77(1H,quint-like,J=6.1Hz),9.74(1H,t,J=1.9Hz); 13 C-NMR (125MHz, CDCl3): δ=9.52,21.18,21.90,25.04,26.89,28.97,29.16,33.44,43.78,75.31,170.91,202.70 [Mass spectrum] EI-mass spectrum (70 eV): m / z 215 (M + +1), 185, 171, 156, 143, 125, 113, 101, 81, 69, 55, 43, 29 [Infrared absorption spectrum] (D-ATR): ν=2968, 2935, 2859, 2719, 1732, 1463, 1373, 1245, 1113, 1020, 956cm -1

[0122] [Example 7] Preparation of 2,9-diacetoxyundecane (4)

[0123] [ka]

[0124] At 15 to 25° C., a tetrahydrofuran solution of methylmagnesium chloride (399.35 g, 1.03 mol as methylmagnesium chloride) was charged into a reactor, and the 8-(acetyloxy)decanal (1:R 1 =CH3, n=1) (67.45g, 0.31mol, purity 98.11%) was added dropwise at 40-60°C, and the mixture was stirred at 30-40°C for 4 hours. Then, acetic anhydride (111.73g, 1.09mol) was added dropwise at 40-60°C, and the mixture was stirred at 30-40°C for 2 hours. Then, water (500.00g) was added and the mixture was separated, and the aqueous layer was removed to obtain an organic layer. Then, the obtained organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 2,9-diacetoxyundecane (4) (80.73g, 0.28mol, purity 95.01%, bp=115.6-122.1°C / 0.080kPa (0.60mmHg)) with a two-step yield of 90.04%.

[0125] The spectral data of the 2,9-diacetoxyundecane (4) obtained above is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.86(3H,t,J=7.3Hz),1.18(3H,d,J=6.5Hz),1.20-1.33(8H,m),1.37-1.6 0(6H,m),2.00(3H,s),2.02(3H,s),4.78(1H,quint-like,J=6.6Hz),4.86(1H,tq,J=6.5Hz,6.5Hz); 13 C-NMR (125MHz, CDCl3): δ=9.53,19.91,21.20,21.33,25.18,25.25,26.90,29.26,29.34,33.50,35.82,70.93,75.40,170.72,170.92 [Mass spectrum] EI-mass spectrum (70 eV): m / z 273 (M ++1), 229, 215, 201, 183, 169, 155, 141, 123, 96, 81, 67, 43, 29 [Infrared absorption spectrum] (D-ATR): νmax = 2971, 2935, 2859, 1737, 1463, 1372, 1244, 1128, 1021, 953 cm -1

[0126] [Example 8] Preparation of 2,9-diacetoxyundecane (4)

[0127] [ka]

[0128] At 15 to 25°C, a tetrahydrofuran solution of ethylmagnesium chloride (816.59 g, 1.67 mol as methylmagnesium chloride) was charged into a reactor, and 8-(acetyloxy)nonanal (1:R) produced under the same conditions as in Example 5 was added. 1 =CH3, n=0) (103.32 g, 0.51 mol, purity 98.08%) was added dropwise at 40-60°C, and the mixture was stirred at 30-40°C for 5 hours. Then, acetic anhydride (180.80 g, 1.77 mol) was added dropwise at 40-60°C, and the mixture was stirred at 30-40°C for 3.5 hours. Then, water (809.14 g) was added and the mixture was separated, and the aqueous layer was removed to obtain an organic layer. Then, the obtained organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 2,9-diacetoxyundecane (4) (122.60 g, 0.42 mol, purity 92.38%, bp=115.6-122.1°C / 0.080 kPa (0.60 mmHg)) with a two-step yield of 82.18%.

[0129] The spectral data of the 2,9-diacetoxyundecane (4) obtained above was the same as that obtained in Example 7.

[0130] [Example 9] 8-(Trimethylacetyloxy)decanal (1:R 1 Preparation of (CH3)3, n=1) [ka]

[0131] At room temperature, 8-hydroxydecanal (11) (4.0 g, 0.023 mol, purity 98.59%) produced under the same conditions as in Comparative Example 1 below, pyridine (2.90 g, 0.037 mol), and acetonitrile (10.00 g) were charged into a reactor and stirred at 15 to 25°C for 14 minutes. Then, pivaloyl chloride (2.76 g, 0.023 mol) was added dropwise at 20 to 30°C, and the mixture was stirred at 20 to 30°C for 8 hours. Then, water (15.00 g) was added and the mixture was separated, and the aqueous layer was removed to obtain an organic layer. The obtained organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1 to 5:1) to obtain 8-(trimethylacetyloxy)decanal (1:R 1 =C(CH3)3, n=1) (2.08 g, 0.0080 mol, 98.24% purity) was obtained in 34.89% yield.

[0132] The 8-(trimethylacetyloxy)decanal (1:R 1 The spectral data for =C(CH3)3, n=1) is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=0.85(3H,t,J=7.3Hz),1.18(9H,s),1.21-1.34(6H,),1.43-1.64( 6H,m),2.40(2H,dt,J=1.9Hz,7.3Hz),4.76(1H,tt,J=7.3Hz,5.3Hz),9.74(1H,t,J=1.9Hz); 13 C-NMR (125MHz, CDCl3): δ=9.48,21.92,25.01,26.93,27.18,28.99,29.17,33.50,38.82,43.80,74.75,178.26,202.72 [Mass spectrum] EI-mass spectrum (70 eV): m / z 257 (M + +1), 227, 213, 199, 171, 155, 137, 95, 81, 57, 41 [Infrared absorption spectrum] (D-ATR): νmax = 2970, 2935, 2860, 2716, 1724, 1480, 1462, 1396, 1367, 1284, 1166, 1113, 1032, 936 cm -1

[0133] [Example 10] 8-(benzoyloxy)decanal (1:R 1 =Ph, n=1) [ka]

[0134] At room temperature, 8-hydroxydecanal (11) (4.0 g, 0.023 mol, purity 98.59%) produced under the same conditions as in Comparative Example 1 below, pyridine (2.90 g, 0.037 mol), and acetonitrile (10.00 g) were charged into a reactor and stirred at 15 to 25°C for 10 minutes. Benzoyl chloride (3.22 g, 0.023 mol) was then added dropwise at 20 to 30°C, and the mixture was stirred at 20 to 30°C for 7 hours. Water (15.00 g) was then added and the mixture was separated, and the aqueous layer was removed to obtain an organic layer. The obtained organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to obtain 8-(benzoyloxy)decanal (1:R 1 =Ph, n=1) (1.13 g, 0.0041 mol, 100% purity) was obtained in 17.80% yield.

[0135] The 8-(benzoyloxy)decanal (1:R 1 The spectral data for (=Ph, n=1) are shown below. [Nuclear Magnetic Resonance Spectrum] 1H-NMR (500MHz, CDCl3): δ=0.94(3H,t,J=7.3Hz),1.26-1.44(6H,m),1,54-1.76(6H,m),2.39(2H,dt,J=1.9Hz,7.3 Hz),5.03-5.10(1H,m),7.43(2H,t-like,J=8.1Hz),7.52-7.57(1H,m),8.02-8.06(2H,m),9.73(1H,t,J=1.9Hz); 13 C-NMR (125MHz, CDCl3): δ=9.61,21.92,25.10,27.06,29.97,29.19,33.56,43.78,75.98,128.27,129.48,130.76,132.68,166.36,202.72 [Mass spectrum] EI-mass spectrum (70 eV): m / z 275 (M + -1), 248, 233, 218, 200, 154, 123, 105, 77, 55, 41 [Infrared absorption spectrum] (D-ATR): ν=2968, 2935, 2858, 2718, 1716, 1602, 1585, 1451, 1275, 1176, 1107, 1070, 1026cm -1

[0136] [Comparative Example 1] Preparation of 8-hydroxynonanal (11)

[0137] [ka]

[0138] At room temperature, the reactor was charged with 9,9-diethoxy-2-nonanol (9A:R 3 =R 4=Et, n=0) (200.00g, 0.84 mol, purity 97.70%), oxalic acid dihydrate (318.04g, 2.52 mol), tetrahydrofuran (840.90g) and water (840.90g) were added and stirred at 60-65°C for 2.5 hours. Then, hexane (494.62g) was added and stirred for 30 minutes. After the stirring was completed, the reaction solution was left to stand and separated, and the aqueous layer was removed to obtain an organic layer. Then, the obtained organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure to obtain 8-hydroxynonanal (11) (18.29g, 0.10 mol, purity 88.26%) in a yield of 12.12%. The yield was extremely low compared to the production method of 8-(acyloxy)alkanal compound (1).

[0139] The spectral data of 8-hydroxynonanal (11) obtained above is shown below. [Nuclear Magnetic Resonance Spectrum] 1 H-NMR (500MHz, CDCl3): δ=1.15(3H,d,J=6.1Hz),1.20-1.49(8H,m),1.56-1.65(2H,m),1 .71(1H,br.s),2.40(2H,dt,J=1.9Hz,7.3Hz),3.71-3.80(1H,m),9.73(1H,t,J=1.9Hz); 13 C-NMR (125MHz, CDCl3): δ=21.90,23.42,25.45,29.02,29.26,39.11,43.78,67.93,202.83 [Mass spectrum] EI-mass spectrum (70 eV): m / z 157 (M + -1), 143, 125, 114, 96, 81, 68, 57, 45, 29 [Infrared absorption spectrum] (D-ATR): ν=3406, 2930, 2857, 1724, 1463, 1373, 1112, 1062, 943cm -1

Claims

1. The following general formula (1): 【Chemistry 1】 (In the formula, n represents 0 or 1, and R １ represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which a hydrogen atom is substituted with one or more halogen atoms. The 8-(acyloxy)alkanal compound represented by the formula:

2. The following general formula (1): 【Chemistry 2】 (In the formula, n represents 0 or 1, and R １ represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which a hydrogen atom is substituted with one or more halogen atoms. with an 8-(acyloxy)alkanal compound (1) represented by the following general formula (2): CH ３ (CH ２ ) （１－ｎ） M １ (2) (In the formula, M １ Li, MgZ １ , CuZ １ Or CuLiZ １ and n represents 0 or 1, where Z １ represents a halogen atom, a methyl group, or an ethyl group. By subjecting the compound to a nucleophilic addition reaction with an alkyl nucleophilic reagent represented by the following formula (3): 【Chemistry 3】 and obtaining 2,9-undecanediol represented by the formula: The 2,9-undecanediol (3) is subjected to an acetylation reaction to obtain a compound represented by the following formula (4): 【Chemistry 4】 and obtaining 2,9-diacetoxyundecane represented by the formula: The method for producing 2,9-diacetoxyundecane (4), comprising at least

3. The following general formula (5): 【Chemistry 5】 (In the formula, n represents 0 or 1; R ３ and R ４ each independently represents a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R ３ and R ４ are bonded to each other ３ -R ４ represents a divalent hydrocarbon group having 2 to 10 carbon atoms, and R １ represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which a hydrogen atom is substituted with one or more halogen atoms. By subjecting a dialkoxyacyloxyalkane compound represented by the following general formula (1): 【Chemistry 6】 (In the formula, n represents 0 or 1, and R １ represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which a hydrogen atom is substituted with one or more halogen atoms. A step of obtaining an 8-(acyloxy)alkanal compound represented by the formula: The method for producing the 8-(acyloxy)alkanal compound (1) comprises at least the steps of:

4. The following general formula (6): 【Chemistry 7】 (In the formula, X represents a halogen atom, R ３ and R ４ each independently represents a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R ３ and R ４ are bonded to each other ３ -R ４ represents a divalent hydrocarbon group having 2 to 10 carbon atoms.) The 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (7): 【Chemistry 8】 (In the formula, M ２ Li, MgZ ２ , CuZ ２ Or CuLiZ ２ where Z ２ represents a halogen atom or a 6,6-dialkoxyhexyl group, and R ３ and R ４ is as defined above.) The 6,6-dialkoxyhexyl nucleophile (7) is converted into a 6,6-dialkoxyhexyl nucleophile represented by the following formula (8): 【Chemistry 9】 By a nucleophilic addition reaction to propylene oxide represented by the following general formula (9A): 【Chemistry 10】 (In the formula, R ３ and R ４ is as defined above.) and obtaining a 9,9-dialkoxy-2-nonanol compound represented by the formula: A step of subjecting the 9,9-dialkoxy-2-nonanol compound (9A) to an acylation reaction to obtain the dialkoxyacyloxyalkane compound (5) (wherein n=0) according to claim 3; The dialkoxyacyloxyalkane compound (5) (wherein n=0) is subjected to a hydrolysis reaction to obtain the 8-(acyloxy)alkanal compound (1) (wherein n=0) according to claim 3. A method for producing an 8-(acyloxy)alkanal compound (1) (wherein n=0), comprising at least

5. The following general formula (6): 【Chemistry 11】 (In the formula, X represents a halogen atom, R ３ and R ４ each independently represents a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R ３ and R ４ are bonded to each other ３ -R ４ represents a divalent hydrocarbon group having 2 to 10 carbon atoms.) The 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (7): 【Chemistry 12】 (In the formula, M ２ Li, MgZ ２ , CuZ ２ Or CuLiZ ２ where Z ２ represents a halogen atom or a 6,6-dialkoxyhexyl group, and R ３ and R ４ is as defined above.) The 6,6-dialkoxyhexyl nucleophile (7) is converted into a 6,6-dialkoxyhexyl nucleophile represented by the following formula (10): 【Chemistry 13】 By nucleophilic addition reaction to 1,2-butylene oxide represented by the following general formula (9B): 【Chemistry 14】 (In the formula, R ３ and R ４ is as defined above.) obtaining a 10,10-dialkoxy-3-decanol compound represented by the formula: A step of subjecting the 10,10-dialkoxy-3-decanol (9B) to an acylation reaction to obtain the dialkoxyacyloxyalkane compound (5) (wherein n=1) according to claim 3; The dialkoxyacyloxyalkane compound (5) (wherein n=1) is subjected to a hydrolysis reaction to obtain the 8-(acyloxy)alkanal compound (1) (wherein n=1) according to claim 3. The method for producing the 8-(acyloxy)alkanal compound (1) (wherein n=1) comprises at least the steps of:

6. The process for producing an 8-(acyloxy)alkanal compound (1) from the dialkoxyacyloxyalkane compound (5) according to claim 3; The process for producing 2,9-diacetoxyundecane (4) from the 8-(acyloxy)alkanal compound (1) according to claim 2. The method for producing 2,9-diacetoxyundecane (4), comprising at least

7. The following general formula (6): 【Chemistry 15】 (In the formula, X represents a halogen atom, R ３ and R ４ each independently represents a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R ３ and R ４ are bonded to each other ３ -R ４ represents a divalent hydrocarbon group having 2 to 10 carbon atoms.) The 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (7): 【Chemistry 16】 (In the formula, M ２ Li, MgZ ２ , CuZ ２ Or CuLiZ ２ where Z ２ represents a halogen atom or a 6,6-dialkoxyhexyl group, and R ３ and R ４ is as defined above.) The 6,6-dialkoxyhexyl nucleophile (7) is converted into a 6,6-dialkoxyhexyl nucleophile represented by the following formula (8): 【Chemistry 17】 By a nucleophilic addition reaction to propylene oxide represented by the following general formula (9A): 【Chemistry 18】 (In the formula, R ３ and R ４ is as defined above.) and obtaining a 9,9-dialkoxy-2-nonanol compound represented by the formula: The 9,9-dialkoxy-2-nonanol compound (9A) is subjected to an acylation reaction to obtain a compound represented by the following general formula (5A): 【Chemistry 19】 (In the formula, R １ , R ３ and R ４ is as defined above.) obtaining a 9,9-dialkoxy-2-acyloxynonane compound represented by the formula: A step of subjecting the 9,9-dialkoxy-2-acyloxynonane compound (5A) to a hydrolysis reaction to obtain the 8-(acyloxy)alkanal compound (1) (wherein n=0) according to claim 2; The method according to claim 2, wherein 2,9-diacetoxyundecane (4) is obtained from the 8-(acyloxy)alkanal compound (1) (wherein n=0). The method for producing 2,9-diacetoxyundecane (4), comprising at least

8. The following general formula (6): 【Chemistry 20】 (In the formula, X represents a halogen atom, R ３ and R ４ each independently represents a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R ３ and R ４ are bonded to each other ３ -R ４ represents a divalent hydrocarbon group having 2 to 10 carbon atoms.) The 6-halo-1,1-dialkoxyhexane compound represented by the following general formula (7): 【Chemistry 21】 (In the formula, M ２ Li, MgZ ２ , CuZ ２ Or CuLiZ ２ where Z ２ represents a halogen atom or a 6,6-dialkoxyhexyl group, and R ３ and R ４ is as defined above.) The 6,6-dialkoxyhexyl nucleophile (7) is converted into a 6,6-dialkoxyhexyl nucleophile represented by the following formula (10): 【Chemical 22】 By nucleophilic addition reaction to 1,2-butylene oxide represented by the following general formula (9B): 【Chemistry 23】 (In the formula, R ３ and R ４ is as defined above.) obtaining a 10,10-dialkoxy-3-decanol compound represented by the formula: The 9,9-dialkoxy-2-nonanol compound (9B) is subjected to an acylation reaction to obtain a compound represented by the following general formula (5B): 【Chemistry 24】 (In the formula, R １ , R ３ and R ４ is as defined above.) obtaining a 10,10-dialkoxy-3-acyloxydecane compound represented by the formula: a step of subjecting the 10,10-dialkoxy-3-acyloxydecane compound (5B) to a hydrolysis reaction to obtain the 8-(acyloxy)alkanal compound (1) (wherein n=1) according to claim 2; The method according to claim 2, wherein the 8-(acyloxy)alkanal compound (1) (wherein n=1) is used to obtain 2,9-diacetoxyundecane (4). The method for producing 2,9-diacetoxyundecane (4), comprising at least

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