Process for the preparation of 1-arylsulfonyloxy-5-haloalkyl compounds and process for the preparation of 6,10,14-trimethyl-2-pentadecanol therefrom

Abstract

The present invention relates to a process for preparing a 1-arylsulfonyloxy-5-haloalkyl compound (3) wherein R 1 and R 2 independently of one another represent a hydrogen atom or a methyl group, and X 1 represents a halogen atom, said process comprising the step of subjecting a tetrahydropyrane compound (1) wherein R 1 represents a hydrogen atom or a methyl group, to an opening reaction with an arylsulfonyl halide compound (2) wherein R 2 represents a hydrogen atom or a methyl group, and X 1 represents a halogen atom, in the presence of zinc chloride, to form the above-mentioned 1-arylsulfonyloxy-5-haloalkyl compound (3).

Description

Technical Field

[0001] The embodiments of the present invention relate to a method for preparing 1-arylsulfonyloxy-5-haloalkane compounds and a method for preparing 6,10,14-trimethyl-2-pentadecanol from the same. Background Technology

[0002] 1-Aromonyloxy-5-haloalkyl compounds can be coupled to form long-chain hydrocarbon skeletons, making them highly useful as synthetic precursors for methyl-branched insect pheromones and insect epidermal hydrocarbon compounds. Known methyl-branched insect pheromones include the rice moth (Corcyra cephalonica) sex pheromone, 6,10,14-trimethyl-2-pentadecanol (see Non-Patent Literature 1 below).

[0003] The following method has been reported for preparing 1-arylsulfonyloxy-5-haloalkanes. The method for preparing 1-arylsulfonyloxy-5-haloalkanes, specifically 1-bromo-3-methyl-5-(p-toluenesulfonyloxy)pentane, includes, for example, reacting 4-methyltetrahydropyran with acetyl bromide in the presence of a zinc chloride catalyst to give 1-acetoxy-5-bromo-3-methylpentane in 89% yield; then, in a methanol solvent, in the presence of a p-toluenesulfonic acid catalyst, eliminating the acetyl group in the resulting 1-acetoxy-5-bromo-3-methylpentane with water to form 5-bromo-3-methyl-1-pentanol in 82% yield (see Non-Patent Literature 2 below). Subsequently, in a pyridine solvent, toluenesulfonating the hydroxyl group of the resulting 5-bromo-3-methyl-1-pentanol with p-toluenesulfonyl chloride to give 1-arylsulfonyloxy-5-haloalkanes in 75% yield (see Non-Patent Literature 3 below).

[0004] Another reported method for preparing 1-aransulfonyloxy-5-haloalkane compounds, 1-chloro-5-(p-toluenesulfonyloxy)pentane, includes, for example, toluenesulfonating the hydroxyl group of 5-chloro-1-pentanol with p-toluenesulfonyl chloride in a pyridine solvent in the presence of a 4-dimethylaminopyridine (DMAP) catalyst, with a yield of 96% (see Non-Patent Literature 4 below).

[0005] Non-patent literature

[0006] [Non-patent literature 1] DR Hall et al., J. Chem. Ecol., 1987, 13 (7), 1575-1589.

[0007] [Non-Patent Literature 2] VN Odinokov et al., Chemistry of Natural Compounds, 1989, 25, 236-239.

[0008] [Non-Patent Literature 3] VN Odinokov et al., Chemistry of Natural Compounds, 1990, 26, 86-87.

[0009] [Non-patent literature 4] K. Mori et al., Tetrahedron, 2010, 66 (14), 2642-2653.

[0010] [Non-patent literature 5] Y. Ishii et al., Journal of the Society of Chemical Industry, Japan, 1966, 69 (7), 1388-1393.

[0011] Purpose of the invention

[0012] However, the methods for preparing 1-arylsulfonyloxy-5-haloalkyl compounds according to Non-Patent Literature 2 and 3 require three steps: ring-opening reaction, acetyl elimination, and arylsulfonyloxylation (toluenesulfonation). Therefore, the number of steps is large, and the overall yield of the three steps is as low as 55%. In addition, the use of large amounts of solvent in the elimination and toluenesulfonation steps increases the environmental impact, and the preparation method is not suitable for industrialization.

[0013] The method for preparing 1-arylsulfonyloxy-5-haloalkane compounds according to Non-Patent Literature 4 is also unsuitable for industrial application because the starting material 5-chloro-1-pentanol is extremely expensive. Furthermore, considering green chemistry, the above preparation method is not preferred because it uses pyridine as a base in large quantities as a solvent.

[0014] This invention addresses the above-mentioned issues and aims to provide a method for the one-step, efficient preparation of 1-arylsulfonyloxy-5-haloalkyl compounds from inexpensive tetrahydropyran compounds. This invention also aims to provide a synthetic intermediate, namely 1-arylsulfonyloxy-5-halo-3-methylpentane, which can be used to synthesize insect pheromone compounds, and to provide a method for preparing the sex pheromone compound 6,10,14-trimethyl-2-pentadecanol. Summary of the Invention

[0015] To overcome the aforementioned problems in the prior art, through in-depth research, the inventors discovered that a one-step, highly efficient method for preparing 1-arylsulfonyloxy-5-haloalkane compounds can be achieved by subjecting a tetrahydropyran compound with a six-membered ring skeleton to a ring-opening reaction with an arylsulfonyl halide compound. Since Non-Patent Literature 5 reports that the reactivity of the tetrahydropyran compound with a six-membered ring skeleton is 100 times lower than that of the tetrahydrofuran compound with a five-membered ring skeleton in the ring-opening reaction, it is surprising that the aforementioned problems can be overcome.

[0016] It was also found that, since the addition of methanol after the ring-opening reaction can achieve excellent phase separation, the 1-arylsulfonyloxy-5-haloalkane compound can be used in subsequent steps without filtration or purification.

[0017] According to one aspect of the present invention, a method for preparing 1-arylsulfonyloxy-5-haloalkane compounds of the following general formula (3) is provided:

[0018]

[0019] Where R 1 and R 2 Each can independently represent a hydrogen atom or a methyl group, and X 1 Represents halogen atoms,

[0020] The method includes the following steps:

[0021] Tetrahydropyran compounds of the following general formula (1):

[0022]

[0023] Where R 1 Indicates a hydrogen atom or a methyl group.

[0024] Ring-opening reaction with aryl sulfonyl halide compounds of general formula (2) in the presence of zinc chloride:

[0025]

[0026] Where R 2 Represents a hydrogen atom or a methyl group, and X 1 Represents halogen atoms,

[0027] To form the above-mentioned 1-aransulfonyloxy-5-haloalkane compound (3).

[0028] According to a second aspect of the present invention, a method for preparing a 1-halo-3,7,11-trimethyldodecane compound of the following general formula (5) is provided:

[0029]

[0030] Where X1 Represents halogen atoms,

[0031] The method includes the following steps:

[0032] The first aspect above refers to the tetrahydropyran compound (1), wherein R 1 =CH3 (hereinafter referred to as tetrahydropyran compound (1:R) 1 =CH3)), a method for preparing 1-arylsulfonyloxy-5-haloalkane compounds (3), wherein R 1 =CH3 (hereinafter referred to as 1-arylsulfonyloxy-5-haloalkyl compound (3:R) 1 =CH3)), and

[0033] Make the nucleophile 2,6-dimethylheptyl compound of the following general formula (4):

[0034]

[0035] Where M 1 Indicates Li, Mg, Z 1 CuZ 1 or CuLiZ 1 And Z 1 This indicates a halogen atom or a 2,6-dimethylheptyl group.

[0036] With 1-arylsulfonyloxy-5-halo-3-methylpentane compounds (3: R 1 =CH3) undergoes a coupling reaction to form the above-mentioned 1-halo-3,7,11-trimethyldodecane compound (5).

[0037] According to a third aspect of the present invention, a method for preparing 6,10,14-trimethyl-2-pentadecanol of formula (8) is provided:

[0038]

[0039] The method includes the following steps:

[0040] The first aspect above refers to the tetrahydropyran compound (1), wherein R 1 =CH3 (hereinafter referred to as tetrahydropyran compound (1:R) 1 =CH3)), the method for preparing the above 1-arylsulfonyloxy-5-haloalkane compound (3), wherein R 1 =CH3 (hereinafter referred to as 1-arylsulfonyloxy-5-haloalkyl compound (3:R) 1 =CH3)),

[0041] Make the nucleophile 2,6-dimethylheptyl compound of the following general formula (4):

[0042]

[0043] Where M 1 Indicates Li, Mg, Z 1 CuZ 1 or CuLiZ 1 And Z 1 This indicates a halogen atom or a 2,6-dimethylheptyl group.

[0044] With 1-arylsulfonyloxy-5-halo-3-methylpentane compounds (3: R 1 =CH3) undergoes a coupling reaction to form a 1-halo-3,7,11-trimethyldodecane compound of the following general formula (5):

[0045]

[0046] Where X 1 Represents halogen atoms,

[0047] The 1-halo-3,7,11-trimethyldodecane compound (5) thus obtained is converted into a nucleophilic 3,7,11-trimethyldodecane compound of the following general formula (6):

[0048]

[0049] Where M 2 Indicates Li, Mg, Z 2 CuZ 2 or CuLiZ 2 And Z 2 Indicates a halogen atom or 3,7,11-trimethyldodecyl.

[0050] as well as

[0051] The nucleophile 3,7,11-trimethyldodecyl compound (6) thus obtained is subjected to a nucleophilic addition reaction with propylene oxide of formula (7):

[0052]

[0053] To form the above-mentioned 6,10,14-trimethyl-2-pentadecanol (8).

[0054] According to the present invention, the target compound 1-arylsulfonyloxy-5-haloalkane can be prepared efficiently with fewer steps, has minimal environmental impact, and achieves high yield. According to the present invention, the target compound 1-arylsulfonyloxy-5-haloalkane can be prepared economically. According to the present invention, purification by column chromatography and / or distillation is unnecessary, thereby allowing impurities to be removed by phase separation, and the method is scalable. According to the present invention, in the 1-arylsulfonyloxy-5-haloalkane compound, a 1-arylsulfonyloxy-5-halo-3-methylpentane compound can be used, wherein R... 1 =CH3, to prepare the above 1-arylsulfonyloxy-5-haloalkane compound and the above 6,10,14-trimethyl-2-pentadecanol. Detailed Implementation

[0055] (I) A method for preparing 1-arylsulfonyloxy-5-haloalkane compounds of the following general formula (3).

[0056] (i) 1-Aromonyloxy-5-haloalkane compounds (3) are represented by the following general formula (3):

[0057] In the above general formula (3), R 1 and R 2 Each can be represented independently by a hydrogen atom or a methyl group, X 1 Represents a halogen atom. Halogen atom X 1 Specific examples include chlorine, bromine, and iodine atoms. Halogen atom X 1 Preferably, chlorine and bromine atoms are used. Preferred reactivity can be ensured by using the chlorine and bromine atoms. Halogen atom X 1 More preferably, it is a chlorine atom. By using the chlorine atom, even better reactivity can be ensured.

[0058] (ii) The preparation method of the above-mentioned 1-arylsulfonyloxy-5-haloalkyl compound (3) will be described in detail below.

[0059] 1-Arylsulfonyloxy-5-haloalkane compound (3) can be prepared by ring-opening reaction of a tetrahydropyran compound of general formula (1) with an arylsulfonyl halide compound of general formula (2) in the presence of zinc chloride, as shown in the following chemical reaction formula:

[0060]

[0061] First, the tetrahydropyran compound (1) will be explained in detail below.

[0062]

[0063] In the above general formula (1), R 1 It represents a hydrogen atom or a methyl group.

[0064] Specific examples of tetrahydropyran compounds (1) include tetrahydropyran (R 1 = H) and 4-methyltetrahydropyran (R 1 =CH3). The tetrahydropyran compound (1) is preferably 4-methyltetrahydropyran. By using the 4-methyltetrahydropyran, it is possible to ensure the preferred preparation of insect pheromones with methyl branches.

[0065] Tetrahydropyran compound (1) can be commercially available.

[0066] The following section will describe the aromatic sulfonyl halide compound (2) in detail.

[0067]

[0068] In the aryl sulfonyl halide compound (2), R 2 Represents a hydrogen atom or a methyl group, and X 1 Represents a halogen atom. Halogen atom X 1 Specific examples include chlorine, bromine, and iodine atoms. Halogen atom X 1 Preferably, chlorine and bromine atoms are used. Preferred reactivity can be ensured by using the chlorine and bromine atoms. Halogen atom X 1 More preferably, it is a chlorine atom. By using the chlorine atom, better reactivity can be ensured.

[0069] Specific examples of aryl sulfonyl halides (2) include benzenesulfonyl halides (R 2 =H), such as benzenesulfonyl chloride, benzenesulfonyl bromide and benzenesulfonyl iodide; and toluenesulfonyl halide compounds (R 2 =CH3), such as toluenesulfonyl chloride, toluenesulfonyl bromide, and toluenesulfonyl iodide. The aryl sulfonyl halide compound (2) is preferably benzenesulfonyl chloride, benzenesulfonyl bromide, toluenesulfonyl chloride, and toluenesulfonyl bromide. Preferred economy and / or processability can be ensured by using said benzenesulfonyl chloride, benzenesulfonyl bromide, toluenesulfonyl chloride, and toluenesulfonyl bromide. The aryl sulfonyl halide compound (2) is more preferably benzenesulfonyl chloride and toluenesulfonyl chloride. Further improved economy and / or processability can be ensured by using said benzenesulfonyl chloride and toluenesulfonyl chloride. The aryl sulfonyl halide compound (2) is even more preferably benzenesulfonyl chloride. Even more improved economy and / or processability can be ensured by using said benzenesulfonyl chloride.

[0070] If necessary, the aryl sulfonyl halide compound (2) may be used alone or in combination. The aryl sulfonyl halide compound (2) may be commercially available.

[0071] For each mol of tetrahydropyran compound (1), the amount of arylsulfonyl halide compound (2) is preferably 0.5 to 2.0 mol, more preferably 0.7 to 1.5 mol, and even more preferably 0.8 to 1.1 mol. By using the preferred, more preferred, and even more preferred amounts, preferred reactivity, and even more preferred reactivity can be ensured. In ring-opening reactions, if 1.3 equivalents or more of tetrahydropyran compound (1) are used per unit of arylsulfonyl halide compound (2), the reaction rate decreases. In ring-opening reactions, if 1.5 equivalents or more of tetrahydropyran compound (1) are used per unit of arylsulfonyl halide compound (2), the reaction rate decreases further. If 2.0 equivalents or more are used, the reaction becomes extremely slow and cannot be completed.

[0072] If necessary, a solvent can be incorporated into the ring-opening reaction.

[0073] Examples of solvents include general solvents such as hydrocarbon solvents, such as hexane, heptane, benzene, toluene, xylene, and cumene. Toluene, xylene, and cumene are preferred solvents. Preferred reactivity can be ensured by using toluene, xylene, and cumene. Toluene and xylene are more preferred solvents. Further preferred reactivity can be ensured by using toluene and xylene.

[0074] Solvents may be used alone or in combination if necessary. Solvents may be commercially available.

[0075] When a solvent is incorporated into the ring-opening reaction, the amount of solvent used is preferably greater than 0 to 3000 g per mol of tetrahydropyran compound (1), more preferably greater than 0 to 800 g.

[0076] Introducing a solvent will significantly reduce the reaction rate, so it is best to carry out a solvent-free reaction without incorporating the aforementioned solvents.

[0077] The reaction temperature for the ring-opening reaction is preferably 60 to 180°C, more preferably 70 to 120°C, and even more preferably 75 to 100°C. By using the preferred reaction temperature, the more preferred reaction temperature, and the even more preferred reaction temperature, preferred reactivity, and even more preferred reactivity can be ensured.

[0078] The reaction time for the ring-opening reaction varies depending on the production scale, preferably from 0.1 to 100 hours, more preferably from 0.3 to 50 hours, and even more preferably from 0.5 to 20 hours. By using the preferred reaction time, the more preferred reaction time, and the even more preferred reaction time, preferred reactivity, and even more preferred reactivity can be ensured.

[0079] Although the 1-arylsulfonyloxy-5-haloalkyl compound (3) can be prepared as described above, the separation between the aqueous and organic layers is extremely poor if the reaction is quenched with an aqueous solution followed by the addition of brine or the like, resulting in a boundary layer between the two layers. This boundary layer persists even after the addition of an extraction solvent, sodium chloride, and / or heating. Therefore, a clean organic layer can be obtained by removing the boundary layer during phase separation, but the loss of the organic layer leads to a reduced yield. On the other hand, if the boundary layer is contained on the organic layer side, a large amount of salt will precipitate after concentration, so the reaction mixture cannot be used directly for subsequent steps and must be filtered or purified by silica gel column chromatography or distillation. However, the separation between the organic and aqueous layers is excellent by adding an alcohol compound (9) after quenching the reaction with an aqueous solution, so the addition of an alcohol compound (9) is preferred. Examples of alcohol compounds (9) include methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-butanol, n-pentanol, ethylene glycol, and propylene glycol. Methanol, ethanol, n-propanol, and isopropanol are preferred for alcohol compounds (9). By using the methanol, ethanol, n-propanol, and isopropanol, preferred separation of the organic layer and the aqueous layer can be ensured. The alcohol compound (9) is more preferably methanol and ethanol. By using the methanol and ethanol, even more preferred separation of the organic layer and the aqueous layer can be ensured. The alcohol compound (9) is even more preferably methanol. By using the methanol, even more preferred separation of the organic layer and the aqueous layer can be ensured.

[0080] For each mol of tetrahydropyran compound (1), the amount of alcohol compound (9) added is preferably greater than 0 to 1000 g, more preferably 15 g to 500 g, even more preferably 30 g to 300 g, and particularly preferably 50 g to 150 g.

[0081] Therefore, by adding alcohol compound (9) in the post-treatment, the separation of the organic and aqueous layers is excellent and no boundary layer is formed. As a result, since phase separation does not lead to loss of the organic layer and there is no salt precipitation after phase separation and concentration, the product 1-arylsulfonyloxy-5-haloalkane compound (3) can be directly incorporated into the reaction in subsequent steps without filtration and / or purification steps.

[0082] In the 1-arylsulfonyloxy-5-haloalkane compound (3) prepared in this way, R 1 and R 2 Represents a hydrogen atom or a methyl group, and X 1 This represents a halogen atom. Here, R is based on the halogen atom in 1-aranyloxy-5-haloalkane compound (3). 1 R in the aryl sulfonyl halide compound (2) used in the ring-opening reaction 2 The combination of R 1 and R 2 Each can be a hydrogen atom, R 1 and R 2Each can be a methyl group, R 1 and R 2 They can be hydrogen atoms and methyl groups, or R 1 and R 2 They can be methyl and hydrogen atoms, respectively.

[0083] Specific examples of 1-arylsulfonyloxy-5-haloalkane compounds (3) include the following compounds:

[0084] 1-Benzenesulfonyloxy-5-halopentane compounds, such as 1-benzenesulfonyloxy-5-chloropentane, 1-benzenesulfonyloxy-5-bromopentane, and 1-benzenesulfonyloxy-5-iodopentane;

[0085] 1-Halo-5-(p-toluenesulfonyloxy)pentane compounds, such as 1-chloro-5-(p-toluenesulfonyloxy)pentane, 1-bromo-5-(p-toluenesulfonyloxy)pentane, and 1-iodo-5-(p-toluenesulfonyloxy)pentane;

[0086] 1-Benzenesulfonyloxy-5-halo-3-methylpentane compounds, such as 1-benzenesulfonyloxy-5-chloro-3-methylpentane, 1-benzenesulfonyloxy-5-bromo-3-methylpentane, and 1-benzenesulfonyloxy-5-iodo-3-methylpentane; and

[0087] 1-Halo-3-methyl-5-(p-toluenesulfonyloxy)pentane compounds, such as 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane, 1-bromo-3-methyl-5-(p-toluenesulfonyloxy)pentane, and 1-iodo-3-methyl-5-(p-toluenesulfonyloxy)pentane.

[0088] The 1-arylsulfonyloxy-5-haloalkane compound (3) is preferably 1-benzenesulfonyloxy-5-chloropentane, 1-benzenesulfonyloxy-5-bromopentane, 1-chloro-5-(p-toluenesulfonyloxy)pentane, 1-bromo-5-(p-toluenesulfonyloxy)pentane, 1-benzenesulfonyloxy-5-chloro-3-methylpentane, 1-benzenesulfonyloxy-5-bromo-3-methylpentane, 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane, and 1-bromo-3-methyl-5-(p-toluenesulfonyloxy)pentane. Preferred reactivity can be ensured by using the aforementioned 1-benzenesulfonyloxy-5-chloropentane, 1-benzenesulfonyloxy-5-bromopentane, 1-chloro-5-(p-toluenesulfonyloxy)pentane, 1-bromo-5-(p-toluenesulfonyloxy)pentane, 1-benzenesulfonyloxy-5-chloro-3-methylpentane, 1-benzenesulfonyloxy-5-bromo-3-methylpentane, 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane, and 1-bromo-3-methyl-5-(p-toluenesulfonyloxy)pentane. The 1-aranylsulfonyloxy-5-haloalkane compound (3) is more preferably 1-benzenesulfonyloxy-5-chloropentane, 1-chloro-5-(p-toluenesulfonyloxy)pentane, 1-benzenesulfonyloxy-5-chloro-3-methylpentane, and 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane. By using the aforementioned 1-benzenesulfonyloxy-5-chloropentane, 1-chloro-5-(p-toluenesulfonyloxy)pentane, 1-benzenesulfonyloxy-5-chloro-3-methylpentane, and 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane, a more desirable reactivity can be ensured. The 1-arylsulfonyloxy-5-haloalkane compound (3) is even more preferably 1-benzenesulfonyloxy-5-chloro-3-methylpentane and 1-benzenesulfonyloxy-5-chloropentane. By using the aforementioned 1-benzenesulfonyloxy-5-chloro-3-methylpentane and 1-benzenesulfonyloxy-5-chloropentane, an even more desirable processability can be ensured. The 1-arylsulfonyloxy-5-haloalkane compound (3) is particularly preferably 1-benzenesulfonyloxy-5-chloro-3-methylpentane. By using the aforementioned 1-benzenesulfonyloxy-5-chloro-3-methylpentane, a particularly desirable processability can be ensured.

[0089] (II) From 1-arylsulfonyloxy-5-haloalkyl compounds (3), wherein R 1 =CH3, i.e., 1-arylsulfonyloxy-5-halo-3-methylpentane compound (3) (hereinafter referred to as 1-arylsulfonyloxy-5-haloalkyl compound (3: R) 1 = CH3)), Method for preparing 1-halo-3,7,11-trimethyldodecane compound (5)

[0090] This can be achieved by making the above 1-arylsulfonyloxy-5-halo-3-methylpentane compound (3:R 1=CH3) was coupled with the nucleophile 2,6-dimethylheptyl compound (4) to prepare 1-halo-3,7,11-trimethyldodecane compound (5), as shown in the following chemical reaction formula:

[0091]

[0092] (a) First, the nucleophile 2,6-dimethylheptyl compound (4) will be described in detail below. The nucleophile 2,6-dimethylheptyl compound (4) is represented by the following general formula (4):

[0093]

[0094] In the above general formula (4), M 1 Indicates Li, MgZ 1 CuZ 1 or CuLiZ 1 And Z 1 This represents a halogen atom or 2,6-dimethylheptyl. Halogen atom Z 1 Specific examples include chlorine, bromine, and iodine atoms. Halogen atoms (Z) 1 Preferably, chlorine and bromine atoms are used. Preferred reactivity can be ensured by using the chlorine and bromine atoms. Halogen atom Z 1 Chlorine atoms are particularly preferred. By using the chlorine atoms, even better reactivity can be ensured.

[0095] Specific examples of nucleophilic 2,6-dimethylheptyl compounds (4) include the following compounds:

[0096] 2,6-Dimethylheptyllithium (where M) 1 = Li);

[0097] 2,6-Dimethylheptylmagnesium halide compounds (where M) 1 =MgZ 1 Examples include 2,6-dimethylheptylmagnesium chloride, 2,6-dimethylheptylmagnesium bromide, and 2,6-dimethylheptylmagnesium iodide (i.e., Grignard reagents);

[0098] Bis(2,6-dimethylheptyl)cuprate compounds (where M) 1 =CuZ 1 ), such as bis(2,6-dimethylheptyl)cuprate; and

[0099] Lithium bis(2,6-dimethylheptyl)copper oxide compound (where M 1 =CuLiZ 1 (e.g., lithium bis(2,6-dimethylheptyl)copper oxide) (i.e., Gilman's reagent).

[0100] The nucleophile 2,6-dimethylheptyl compound (4) is preferably a Grignard reagent such as 2,6-dimethylheptyl magnesium halide. Preferred reactivity can be ensured by using the 2,6-dimethylheptyl magnesium halide compound.

[0101] (b) The preparation method of the above nucleophile 2,6-dimethylheptyl compound (4) will be described in detail below.

[0102] The nucleophile 2,6-dimethylheptyl compound (4) can be prepared, for example, from a 1-halo-2,6-dimethylheptane compound of the following general formula (10):

[0103]

[0104] In the above general formula (10), X 2 Represents a halogen atom. Halogen atom X 2 Specific examples include chlorine, bromine, and iodine atoms. Halogen atom X 2 Preferably, chlorine and bromine atoms are used. Preferred reactivity can be ensured by using the chlorine and bromine atoms. Halogen atom X 2 More preferably, it is a chlorine atom. By using the chlorine atom, better reactivity can be ensured.

[0105] Specific examples of the 1-halo-2,6-dimethylheptane compound (10) include 1-chloro-2,6-dimethylheptane, 1-bromo-2,6-dimethylheptane, and 1-iodo-2,6-dimethylheptane. The 1-halo-2,6-dimethylheptane compound (10) is preferably 1-chloro-2,6-dimethylheptane and 1-bromo-2,6-dimethylheptane. Preferred reactivity can be ensured by using the aforementioned 1-chloro-2,6-dimethylheptane and 1-bromo-2,6-dimethylheptane. The 1-halo-2,6-dimethylheptane compound (10) is more preferably 1-chloro-2,6-dimethylheptane. Further preferred reactivity can be ensured by using the aforementioned 1-chloro-2,6-dimethylheptane.

[0106] The preparation of the nucleophile 2,6-dimethylheptyl compound (4) will be described in detail as an example, wherein M 1 MgZ 1 That is, 2,6-dimethylheptylmagnesium halide reagent (4: M 1 =MgZ 1 (i.e., Grignard reagent) method.

[0107] Grignard reagents, such as magnesium halide 2,6-dimethylheptane (4:M), can be prepared by reacting the above-mentioned 1-halo-2,6-dimethylheptane compound (10) with magnesium in a solvent. 1 =MgZ 1As shown in the following chemical reaction formula:

[0108]

[0109] Preparation of 2,6-dimethylheptylmagnesium halide reagent (4: M 1 =MgZ 1 When ), the amount of magnesium used per mol of 1-halo-2,6-dimethylheptane compound (10) is preferably 1.0 to 2.0 g atoms. By using the preferred amount, the optimal completeness of the reaction can be ensured.

[0110] Examples of solvents include general solvents, such as ether solvents like tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, butyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; and hydrocarbon solvents like hexane, heptane, benzene, toluene, xylene, and cumene. The solvents are preferably hydrocarbon solvents like toluene and xylene; and ether solvents like tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. By using said hydrocarbon solvents, such as toluene and xylene; and ether solvents, such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran, a preferred reaction rate for preparing the above-described Grignard reagent can be ensured. The solvents are more preferably tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. By using said tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran, a more preferred reaction rate for preparing the above-described Grignard reagent can be ensured.

[0111] Solvents can be used alone or in combination if needed. Solvents can be commercially available.

[0112] For each mol of 1-halo-2,6-dimethylheptane compound (10), the amount of solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, and even more preferably 100 to 1000 g. By using the preferred amount, the more preferred amount, and the even more preferred amount, preferred reactivity, and even more preferred reactivity can be ensured.

[0113] The reaction temperature varies depending on the solvent used, and is preferably 30 to 120°C, more preferably 50 to 100°C, and even more preferably 60 to 80°C. By using the preferred reaction temperature, the more preferred reaction temperature, and the even more preferred reaction temperature, preferred reactivity, and even more preferred reactivity can be ensured.

[0114] The reaction time varies depending on the solvent used and / or the production scale, and is preferably from 0.5 to 100 hours. By using the preferred reaction time, optimal reactivity can be ensured.

[0115] (c) The nucleophile 2,6-dimethylheptyl compound (4) and 1-arylsulfonyloxy-5-halo-3-methylpentane compound (3:R) will be described in detail below. 1 Coupling reaction of (=CH3).

[0116] In the coupling reaction, each mol of nucleophile 2,6-dimethylheptyl compound (4), 1-arylsulfonyloxy-5-halo-3-methylpentane compound (3: R 1 The amount of (=CH3) is preferably 0.7 to 2.0 mol, more preferably 0.8 to 1.7 mol, and even more preferably 0.9 to 1.4 mol. By using the preferred amount, the more preferred amount, and the even more preferred amount, preferred economy, and even more preferred economy can be ensured.

[0117] If necessary, a solvent can be incorporated into the coupling reaction. Examples of solvents include general solvents such as ether solvents, such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, butyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; and polar solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), N-methylpyrrolidone (NMP), and dimethyl sulfoxide (DMSO). The solvents used are 1,3-butyrolactone (GBL), acetonitrile, N,N'-dimethylacrylurea (DMPU), hexamethylphosphoric triamine (HMPA), dichloromethane, and chloroform. Preferably, the solvents are hydrocarbon solvents, such as toluene and xylene; and ether solvents, such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. Preferred reactivity can be ensured by using the hydrocarbon solvents, such as toluene and xylene; and the ether solvents, such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. More preferably, the solvents are tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. Even better reactivity can be ensured by using the tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran.

[0118] Solvents can be used alone or in combination if needed. Solvents can be commercially available.

[0119] For each mol of the nucleophile 2,6-dimethylheptyl compound (4), the amount of solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, and even more preferably 100 to 1000 g. By using the preferred amount, the more preferred amount, and the even more preferred amount, preferred reactivity, and even more preferred reactivity can be ensured.

[0120] If desired, the nucleophile 2,6-dimethylheptyl compound (4) and 1-arylsulfonyloxy-5-halo-3-methylpentane compound (3: R 1 The coupling reaction of (=CH3) can be carried out in the presence of a catalyst.

[0121] Examples of catalysts include copper compounds, such as cuprous halides, such as cuprous chloride, cuprous bromide, and cuprous iodide, and copper halides, such as copper chloride, copper bromide, and copper iodide; iron compounds, such as ferrous(II) chloride, ferric(III) chloride, ferrous(II) bromide, ferric(III) bromide, ferrous(II) iodide, ferric(III) iodide, and ferric acetylacetone(III); silver compounds, such as silver chloride, silver nitrate, and silver acetate; titanium compounds, such as titanium tetrachloride, titanium tetrabromide, titanium methoxide(IV), titanium ethoxide(IV), titanium isopropoxide(IV), and titanium oxide(IV); palladium(II) compounds, such as dichlorobis(triphenylphosphine)palladium and dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium; and nickel compounds, such as nickel chloride, dichloro[1,2-bis(diphenylphosphine)ethane]nickel(II), and dichlorobis(triphenylphosphine)nickel(II). Copper compounds are preferred as catalysts. By using the copper compound, preferred reactivity and / or economy can be ensured. Copper halides, such as copper chloride, copper bromide, and copper iodide, are more preferred catalysts. By using the copper halides, such as copper chloride, copper bromide, and copper iodide, even better reactivity and / or economy can be ensured.

[0122] The catalyst can be used alone or in combination if needed. The catalyst can be commercially available.

[0123] For each mol of 1-halo-2,6-dimethylheptane compound (10), the amount of catalyst used is preferably 0.0001 to 1.0 mol, more preferably 0.0005 to 0.5 mol, and even more preferably 0.001 to 0.3 mol. By using the preferred amount, the more preferred amount, and the even more preferred amount, a preferred reaction rate and / or post-treatment, a more preferred reaction rate and / or post-treatment, and even a more preferred reaction rate and / or post-treatment can be ensured.

[0124] When the coupling reaction is carried out in the presence of a catalyst, a co-catalyst may be used if desired. Examples of co-catalysts 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, tri-p-tolylphosphine, and 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl (BINAP). The co-catalyst is preferably a trialkyl phosphite. Preferred reactivity can be ensured by using the trialkyl phosphite. Triethyl phosphite is more preferably a co-catalyst. Further preferred reactivity can be ensured by using the triethyl phosphite.

[0125] If needed, the co-catalyst can be used alone or in combination. The co-catalyst can be commercially available.

[0126] For each mol of 1-halo-2,6-dimethylheptane compound (10), the amount of co-catalyst is preferably 0.0001 to 1.0 mol, more preferably 0.0005 to 0.5 mol, and even more preferably 0.001 to 0.3 mol.

[0127] When the coupling reaction is carried out in the presence of a catalyst, a lithium salt may be incorporated if desired. The lithium salt may be incorporated into the coupling reaction along with the aforementioned co-catalyst, or it may be incorporated alone without the aforementioned co-catalyst. Examples of lithium salts include lithium halides, such as lithium chloride, lithium bromide, and lithium iodide; lithium nitrate; and lithium carbonate. Lithium halides, such as lithium chloride; and lithium nitrate are preferred. Preferred reactivity can be ensured by using said lithium halides, such as lithium chloride; and lithium nitrate.

[0128] Lithium salts can be used alone or in combination if needed. Lithium salts are commercially available.

[0129] In the coupling reaction, the amount of lithium salt used per mol of 1-halo-2,6-dimethylheptane compound (10) is preferably 0.0001 to 1.0 mol, more preferably 0.0005 to 0.5 mol, and even more preferably 0.001 to 0.3 mol. By using the preferred amount, the more preferred amount, and the even more preferred amount, preferred reactivity, and even more preferred reactivity can be ensured.

[0130] The reaction temperature of the coupling reaction varies depending on the nucleophile 2,6-dimethylheptyl compound (4) used, and is preferably -78 to 100°C, more preferably -25 to 70°C, even more preferably -10 to 50°C, and particularly preferably 10 to 35°C. By using the preferred reaction temperature, the more preferred reaction temperature, the even more preferred reaction temperature, and the particularly preferred reaction temperature, preferred reactivity, more preferred reactivity, even more preferred reactivity, and particularly preferred reactivity can be ensured.

[0131] The reaction time for the coupling reaction varies depending on the solvent used and / or the production scale, and is preferably from 0.5 to 100 hours. By using the preferred reaction time, preferred reactivity can be ensured.

[0132] (III) The preparation method of 6,10,14-trimethyl-2-pentadecanol (8) will be described in detail below.

[0133] 6,10,14-trimethyl-2-pentadecanol (8) can be prepared by converting 1-halo-3,7,11-trimethyldodecane compound (5) into the nucleophile 3,7,11-trimethyldodecane compound (6), and then subjecting the nucleophile 3,7,11-trimethyldodecane compound (6) to a nucleophilic addition reaction with propylene oxide (7), as shown in the following chemical reaction formula:

[0134]

[0135] (a) First, the above-mentioned nucleophile 3,7,11-trimethyldodecyl compound (6) will be described in detail below. The nucleophile 3,7,11-trimethyldodecyl compound (6) is represented by the following general formula (6):

[0136]

[0137] In the above general formula (6), M 2 Indicates Li, MgZ 2 CuZ 2 or CuLiZ 2 And Z 2 This indicates a halogen atom or 3,7,11-trimethyldodecyl. Halogen atom Z 2 Specific examples include chlorine, bromine, and iodine atoms. Halogen atoms (Z) 2 Preferably, chlorine and bromine atoms are used. Preferred reactivity can be ensured by using the chlorine and bromine atoms. Halogen atom Z 2 A chlorine atom is particularly preferred. By using the chlorine atom, particularly preferred reactivity can be ensured.

[0138] Specific examples of nucleophiles 3,7,11-trimethyldodecyl compounds (6) include the following compounds:

[0139] 3,7,11-Trimethyldodecyllithium (where M 2 = Li);

[0140] 3,7,11-Trimethyldodecyl magnesium halide compounds (where M 2 =MgZ 2 Examples include 3,7,11-trimethyldodecyl magnesium chloride, 3,7,11-trimethyldodecyl magnesium bromide, and 3,7,11-trimethyldodecyl magnesium iodide (i.e., Grignard reagents);

[0141] Bis(3,7,11-trimethyldodecyl)cuprate compounds (where M 2 =CuZ 2 ), such as bis(3,7,11-trimethyldodecyl)cuprate; and

[0142] Lithium bis(3,7,11-trimethyldodecyl)copper oxide compound (where M 2 =CuLiZ 2 (e.g., lithium bis(3,7,11-trimethyldodecyl)copper oxide) (i.e., Gilman's reagent).

[0143] The nucleophile 3,7,11-trimethyldodecyl compound (6) is preferably a Grignard reagent such as a 3,7,11-trimethyldodecyl magnesium halide compound. Preferred reactivity can be ensured by using the Grignard reagent such as a 3,7,11-trimethyldodecyl magnesium halide compound. More preferably, the nucleophile 3,7,11-trimethyldodecyl compound (6) is 3,7,11-trimethyldodecyl magnesium chloride and 3,7,11-trimethyldodecyl magnesium bromide. Further reactivity can be ensured by using the 3,7,11-trimethyldodecyl magnesium chloride and 3,7,11-trimethyldodecyl magnesium bromide. Even more preferably, the nucleophile 3,7,11-trimethyldodecyl compound (6) is 3,7,11-trimethyldodecyl magnesium chloride. Even more preferably, reactivity can be ensured by using the 3,7,11-trimethyldodecyl magnesium chloride.

[0144] (b) The preparation method of the above nucleophile 3,7,11-trimethyldodecyl compound (6) will be described in detail below.

[0145] The nucleophile 3,7,11-trimethyldodecyl compound (6) can be prepared from the above-mentioned 1-halo-3,7,11-trimethyldodecyl compound (5):

[0146] This will be explained in detail with examples, such as the nucleophile 3,7,11-trimethyldodecyl compound (6), where M 2 MgZ 2 , namely 3,7,11-trimethyldodecyl magnesium halide reagent (6: M 2 =MgZ 2 Preparation method of Grignard reagent (i.e., Grignard reagent).

[0147] Grignard reagent 3,7,11-trimethyldodecyl magnesium halide reagent (6: M) can be prepared, for example, by reacting the above-mentioned 1-halo-3,7,11-trimethyldodecane compound (5) with magnesium in a solvent. 2 =MgZ 2 As shown in the following chemical reaction formula:

[0148]

[0149] When preparing the 3,7,11-trimethyldodecyl magnesium halide reagent (6), the amount of magnesium used per mol of 1-halo-3,7,11-trimethyldodecane compound (5) is preferably 1.0 to 2.0 g atoms. By using the preferred amount, the optimal completeness of the reaction can be ensured.

[0150] Examples of solvents include general solvents, such as ether solvents like tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, butyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; and hydrocarbon solvents like hexane, heptane, benzene, toluene, xylene, and cumene. The solvents are preferably hydrocarbon solvents like toluene and xylene; and ether solvents like tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. By using said hydrocarbon solvents, such as toluene and xylene; and ether solvents, such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran, a preferred reaction rate for preparing the above-described Grignard reagent can be ensured. The solvents are more preferably tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. By using said tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran, a more preferred reaction rate for preparing the above-described Grignard reagent can be ensured.

[0151] Solvents can be used alone or in combination if needed. Solvents can be commercially available.

[0152] For each mol of 1-halo-3,7,11-trimethyldodecane compound (5), the amount of solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, and even more preferably 100 to 1000 g. By using the preferred amount, the more preferred amount, and the even more preferred amount, preferred reactivity, and even more preferred reactivity can be ensured.

[0153] The reaction temperature varies depending on the solvent used, and is preferably 30 to 120°C, more preferably 50 to 100°C, and even more preferably 60 to 80°C. By using the preferred reaction temperature, the more preferred reaction temperature, and the even more preferred reaction temperature, preferred reactivity, and even more preferred reactivity can be ensured.

[0154] The reaction time varies depending on the solvent used and / or the production scale, and is preferably from 0.5 to 100 hours. By using the preferred reaction time, optimal reactivity can be ensured.

[0155] (c) The nucleophilic addition reaction of the nucleophile 3,7,11-trimethyldodecyl compound (6) with propylene oxide (7) will be described in detail below.

[0156] In the nucleophilic addition reaction, the amount of propylene oxide (7) per mol of the nucleophile 3,7,11-trimethyldodecyl compound (6) is preferably 0.8 to 2.0 mol, more preferably 0.9 to 1.7 mol, and even more preferably 1.0 to 1.5 mol. By using the preferred amount, the more preferred amount, and the even more preferred amount, preferred economy, and even more preferred economy can be ensured.

[0157] If desired, a solvent can be incorporated into the nucleophilic addition reaction. Examples of solvents include general solvents such as ether solvents, such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), diethyl ether, butyl ether, 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether, and 1,4-dioxane; hydrocarbon solvents such as hexane, heptane, benzene, toluene, xylene, and cumene; and polar solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), N-methylpyrrolidone (NMP), and dimethyl sulfoxide (DMSO). The solvents used are 1,3-butyrolactone (GBL), acetonitrile, N,N'-dimethylacrylurea (DMPU), hexamethylphosphoric triamine (HMPA), dichloromethane, and chloroform. Preferably, the solvents are hydrocarbon solvents, such as toluene and xylene; and ether solvents, such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. Preferred reactivity can be ensured by using the hydrocarbon solvents, such as toluene and xylene; and the ether solvents, such as tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. More preferably, the solvents are tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran. Even better reactivity can be ensured by using the tetrahydrofuran, 2-methyltetrahydrofuran, and 4-methyltetrahydropyran.

[0158] Solvents can be used alone or in combination if needed. Solvents can be commercially available.

[0159] When a solvent is incorporated into the nucleophilic addition reaction, the amount of solvent used is preferably 30 to 5000 g, more preferably 50 to 3000 g, and even more preferably 100 to 1000 g per mol of the nucleophile 3,7,11-trimethyldodecyl compound (6). By using the preferred amount, the more preferred amount, and the even more preferred amount, preferred reactivity, and even more preferred reactivity can be ensured.

[0160] If desired, the nucleophilic addition reaction can be carried out in the presence of a catalyst.

[0161] Examples of catalysts include copper compounds such as cuprous halides, such as cuprous chloride, cuprous bromide, and cuprous iodide, and copper halides, such as copper chloride, copper bromide, and copper iodide. The catalyst is preferably a cuprous halide. Preferred reactivity can be ensured by using said cuprous halide. Cuprous chloride is more preferably a catalyst. Further preferred reactivity can be ensured by using said cuprous chloride.

[0162] The catalyst can be used alone or in combination if needed. The catalyst can be commercially available.

[0163] For each mol of the nucleophile 3,7,11-trimethyldodecyl compound (6), the amount of catalyst is preferably 0.0001 to 1.0 mol, more preferably 0.0005 to 0.3 mol, and even more preferably 0.001 to 0.1 mol. By using the preferred amounts, the more preferred amounts, and the even more preferred amounts, preferred reaction rates and / or post-treatments, more preferred reaction rates and / or post-treatments, and even more preferred reaction rates and / or post-treatments can be ensured.

[0164] The reaction temperature of the nucleophilic addition reaction varies depending on the nucleophile 3,7,11-trimethyldodecyl compound (6) used, and is preferably -78 to 70°C, more preferably -20 to 50°C, and even more preferably 0 to 30°C. By using the preferred reaction temperature, the more preferred reaction temperature, and the even more preferred reaction temperature, preferred reactivity, and even more preferred reactivity can be ensured.

[0165] The reaction time for the nucleophilic addition reaction varies depending on the solvent used and / or the production scale, and is preferably from 0.5 to 100 hours. By using the preferred reaction time, preferred reactivity can be ensured.

[0166] Therefore, according to the technical solution of the present invention, 1-arylsulfonyloxy-5-haloalkane compound (3) can be prepared easily and efficiently. According to the technical solution of the present invention, 1-arylsulfonyloxy-5-haloalkane compound (3), wherein R... 1 =CH3, i.e., 1-arylsulfonyloxy-5-halo-3-methylpentane compound (3:R 1 =CH3) to prepare the sex pheromone 6,10,14-trimethyl-2-pentadecanol (8) of the rice moth (scientific name: Corcyra cephalonica).

[0167] Example

[0168] The present invention is described with reference to the following embodiments. It should be noted that the present invention is not limited to or not restricted by these embodiments.

[0169] Unless otherwise stated, the term "purity" as used herein refers to the percentage of area in gas chromatography (GC). The term "product ratio" refers to the ratio of the percentage of area in GC. The term "yield" is calculated from the percentage of area determined by GC.

[0170] In the embodiments, reaction monitoring and yield calculation were performed under the following GC conditions.

[0171] GC conditions: GC: GC-2014 capillary gas chromatograph (Shimadzu Corporation); 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: 100℃, rising at a rate of 5℃ / min, up to 230℃.

[0172] Taking into account the purity (%GC) of the starting materials and products, the yield is calculated according to the following equation.

[0173] Yield (%) = {[(weight of product obtained through reaction × %GC) / molecular weight of product]} [(Weight of starting material in reaction × %GC) / Molecular weight of starting material] × 100

[0174] THF stands for tetrahydrofuran, MTHP stands for 4-methyltetrahydropyran, Ph stands for phenyl, and Ts stands for toluenesulfonyl.

[0175] Example 1: 1-Benzenesulfonyloxy-5-chloro-3-methylpentane (3:R) 1 =CH3, R 2 =H, X 1 Preparation of Cl)

[0176]

[0177] At room temperature, zinc chloride (2.18 g, 0.016 mol) and benzenesulfonyl chloride (35.32 g, 0.20 mol) were placed in a reactor and stirred at 85–90 °C for 36 minutes. Then, 4-methyltetrahydropyran (1:R) was added dropwise to the reactor at 85–95 °C. 1=CH3)(22.04 g, 0.22 mol, 100% purity). After the addition was complete, the reaction mixture was stirred at 85 to 90 °C for 9 hours. Then, brine (prepared from sodium chloride (25.30 g) and water (80.00 g)) was added to the reaction mixture, followed by 4-methyltetrahydropyran (20.00 g), then methanol (20.00 g), and the reaction mixture was stirred for another 30 minutes. After stirring, the reaction mixture was transferred to a separatory funnel. The reaction mixture was allowed to stand, and the separation of the organic and aqueous layers was checked after 1 minute and then after 30 minutes. The separation was good at 1 minute and 30 minutes, and no boundary layer was observed (absent). After the reaction mixture was allowed to stand for 30 minutes, phase separation was performed, and the organic layer thus obtained was concentrated under reduced pressure to form 1-benzenesulfonyloxy-5-chloro-3-methylpentane (3:R 1 =CH3, R 2 =H, X 1 =Cl)(51.32 g, 0.16 mol, purity 88.84%), yield 82.36%. Thus obtained 1-benzenesulfonyloxy-5-chloro-3-methylpentane (3:R 1 =CH3, R 2 =H, X 1 The concentrated solution of Cl) contains no solids or residues and the liquid is not cloudy.

[0178] The following is an example of 1-benzenesulfonyloxy-5-chloro-3-methylpentane (3:R) thus obtained. 1 =CH3, R 2 =H, X 1 =Cl) spectral data.

[0179] Nuclear magnetic resonance spectroscopy: 1 H-NMR (500 MHz, CDCl3): δ= 0.85 (3H, d, J = 6.5 Hz), 1.40-1.86 (5H, m), 3.42-3.62 (2H, m), 4.05-4.14 (2H, m), 7.56 (2H, t-like, J= 7.3 Hz), 7.66 (1H, tt, J = 7.7 Hz, 1.6 Hz), 7.91 (2H, d-like, J = 7.8 Hz); 13 C-NMR (125 MHz, CDCl3): δ = 18.41, 26.92, 35.30, 39.16, 42.50, 68.62,127.80, 129.23, 133.73, 136.07.

[0180] Mass spectrometry: EI-mass spectrometry (70 eV): m / z 244 (M + -32), 229, 213, 199, 185, 159, 141,118, 94, 77, 55, 41.

[0181] Infrared absorption spectrum (D-ATR): ν = 2963, 2932, 1449, 1360, 1187, 1097, 945,893, 755, 689, 590.

[0182] Example 2: 1-Benzenesulfonyloxy-5-chloro-3-methylpentane (3:R) 1 =CH3, R 2 =H, X 1 Preparation of Cl)

[0183]

[0184] The reaction mixture was prepared in the same manner as in Example 1, including scale, until the reaction was completed in 9 hours. A brine solution (prepared from sodium chloride (25.30 g) and water (80.00 g)) was then added to the reaction mixture, followed by 4-methyltetrahydropyran (20.00 g), and the reaction mixture was stirred for 30 minutes. After stirring, the reaction mixture was transferred to a separatory funnel. Specifically, unlike in Example 1, methanol (20.00 g) was not added. The reaction mixture was allowed to stand, and the degree of separation between the organic and aqueous layers was verified after 1 minute and then after 30 minutes. At 1 minute and 30 minutes, the separation was unsatisfactory, and a turbid boundary layer remained. After allowing the reaction mixture to stand for 30 minutes, the boundary layer remained on the organic layer side, and phase separation was performed. The organic layer thus obtained was then concentrated under reduced pressure to form 51.74 g of 1-benzenesulfonyloxy-5-chloro-3-methylpentane (3:R 1 =CH3,R 2 =H, X 1 =Cl). However, the liquid thus obtained is a suspension containing a large amount of precipitated solids, which appear to be salts of the reaction products, and therefore is filtered using a glass filter to form 1-benzenesulfonyloxy-5-chloro-3-methylpentane (3:R). 1 =CH3, R 2 =H, X 1 =Cl)(50.73 g, 0.16 mol, purity 90.01%), yield 82.49%.

[0185] Thus obtained 1-benzenesulfonyloxy-5-chloro-3-methylpentane (3:R 1 =CH3, R 2=H, X 1 The polynomial spectral data of =Cl) are the same as those in Example 1.

[0186] Example 3: 1-Chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane (3:R) 1 =CH3, R 2 =CH3, X 1 Preparation of Cl)

[0187]

[0188] A reaction similar to that in Example 1 was performed, but under the conditions that benzenesulfonyl chloride (35.32 g, 0.20 mol) was replaced with p-toluenesulfonyl chloride (38.13 g, 0.20 mol). The reaction mixture was transferred to a separatory funnel and allowed to stand. The separation of the organic and aqueous layers was checked after 1 minute and then after 30 minutes. The separation was good at 1 minute and 30 minutes, with no boundary layer observed. After allowing the reaction mixture to stand for 30 minutes, phase separation was performed, and the organic layer thus obtained was concentrated under reduced pressure to form 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane (3:R 1 =CH3, R 2 =CH3, X 1 =Cl)(53.41 g, 0.17 mol, purity 93.60%), yield 85.96%. Thus obtained 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane (3:R 1 =CH3,R 2 =CH3, X 1 The concentrated solution of Cl) contains no solids or residues and the liquid is not cloudy.

[0189] The following is an example of 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane (3:R) thus obtained. 1 =CH3, R 2 =CH3,X 1 =Cl) spectral data.

[0190] Nuclear magnetic resonance spectroscopy: 1 H-NMR (500 MHz, CDCl3): δ=0.85(3H, d, J=6.5 Hz), 1.40-1.87(5H, m), 2.45(3H, s), 3.42-3.62(2H, m), 4.02-4.11(2H, m), 7.35(2H, d, J=8.0Hz), 7.79(2H, d, J=8.0 Hz); 13C-NMR (125 MHz, CDCl3): δ=18.43, 21.60, 26.93,35.28, 39.15, 42.53, 68.38, 127.84, 129.83, 132.98, 144.78.

[0191] Mass spectrometry: EI-mass spectrometry (70 eV): m / z 290 (M + ), 227, 213, 199, 173, 155, 118, 91,69, 55, 41.

[0192] Infrared absorption spectrum (D-ATR): ν=2963, 2931, 1598, 1457, 1359, 1176, 1097, 946, 891, 816, 664, 555.

[0193] Example 4: 1-Chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane (3:R) 1 =CH3, R 2 =CH3, X 1 Preparation of Cl)

[0194]

[0195] The reaction mixture was prepared in the same manner as in Example 3, including scale, until the reaction was completed in 9 hours. A brine solution (prepared from sodium chloride (25.30 g) and water (80.00 g)) was then added to the reaction mixture, followed by 4-methyltetrahydropyran (20.00 g), and the reaction mixture was stirred for 30 minutes. After stirring, the reaction mixture was transferred to a separatory funnel. Specifically, unlike in Example 3, methanol (20.00 g) was not added. The reaction mixture was allowed to stand, and the degree of separation between the organic and aqueous layers was verified after 1 minute and then after 30 minutes. At 1 minute and 30 minutes, the separation was unsatisfactory, and a turbid boundary layer remained. After allowing the reaction mixture to stand for 30 minutes, the boundary layer remained on the organic layer side, and phase separation was performed. The organic layer thus obtained was then concentrated under reduced pressure to form 52.30 g of 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane (3:R 1 =CH3, R 2 =CH3, X 1 =Cl). However, the liquid thus obtained has a large amount of precipitated solids suspended in it, which appear to be salts of the reaction products, so it is filtered using a glass filter to form 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane (3:R). 1 =CH3, R 2 =CH3, X1 =Cl) (50.17 g, 0.16 mol, purity 92.91%), yield 80.15%.

[0196] Thus obtained 1-chloro-3-methyl-5-(p-toluenesulfonyloxy)pentane (3:R 1 =CH3, R 2 =CH3, X 1 The polynomial spectral data of =Cl) are the same as those in Example 3.

[0197] Example 5: 1-Benzenesulfonyloxy-5-chloropentane (3:R 1 =H, R 2 =H, X 1 Preparation of Cl)

[0198]

[0199] A reaction similar to that in Example 1 was carried out, but under the conditions of 4-methyltetrahydropyran (1:R). 1 =CH3)(22.04 g, 0.22 mol, 100% purity) was reacted with tetrahydropyran (1:R 1 =H)(18.95 g, 0.22 mol, 100% purity) was substituted, and after the reaction was quenched, the 4-methyltetrahydropyran (20.00 g) to be added was replaced with tetrahydropyran (20.00 g). The reaction mixture was transferred to a separatory funnel and allowed to stand. The separation of the organic and aqueous layers was checked after 1 minute and then after 30 minutes. The separation was good at 1 minute and 30 minutes, with no boundary layer observed. After allowing the reaction mixture to stand for 30 minutes, phase separation was performed, and the organic layer thus obtained was concentrated under reduced pressure to form 1-benzenesulfonyloxy-5-chloropentane (3:R 1 =H, R 2 =H, X 1 =Cl)(47.77 g, 0.16 mol, purity 88.80%), yield 80.72%. Thus obtained 1-benzenesulfonyloxy-5-chloropentane (3:R 1 =H, R 2 =H, X 1 The concentrated solution of Cl) contains no solids or residues and the liquid is not cloudy.

[0200] The following is an example of 1-benzenesulfonyloxy-5-chloropentane (3:R) obtained in this way. 1 =H, R 2 =H, X 1 =Cl) spectral data.

[0201] Nuclear magnetic resonance spectroscopy: 1H-NMR(500 MHz, CDCl3): δ=1.42-1.50(2H, m), 1.64-1.75(4H,m), 3.47(2H, t, J=6.5 Hz), 4.06(2H, t, J=6.5 Hz), 7.56(2H, t-like, J=7.3 Hz),7.66(1H, ddt, J=7.3 Hz, 7.3 Hz, 1.2 Hz), 7.89-7.92(2H, m); 13 C-NMR (125 MHz, CDCl3): δ=18.43, 21.60, 26.93, 35.28, 39.15, 42.53, 68.38, 127.84, 129.83,132.98, 144.78.

[0202] Mass spectrometry: EI-mass spectrometry (70 eV): m / z 262 (M + ), 213, 159, 141, 94, 77, 51.

[0203] Infrared absorption spectrum (D-ATR): ν=2956, 1448, 1361, 1187, 1097, 947, 822, 756, 689, 590.

[0204] Example 6: 1-Benzenesulfonyloxy-5-chloropentane (3:R) 1 =H, R 2 =H, X 1 Preparation of Cl)

[0205]

[0206] The reaction mixture was prepared in the same manner as in Example 5, including scale, until the reaction was completed in 9 hours. A brine solution (prepared from sodium chloride (25.30 g) and water (80.00 g)) was then added to the reaction mixture, followed by tetrahydropyran (20.00 g), and the reaction mixture was stirred for 30 minutes. After stirring, the reaction mixture was transferred to a separatory funnel. Specifically, unlike in Example 5, methanol (20.00 g) was not added. The reaction mixture was allowed to stand, and the degree of separation between the organic and aqueous layers was verified after 1 minute and then after 30 minutes. At 1 minute and 30 minutes, the separation was unsatisfactory, and a turbid boundary layer remained. After allowing the reaction mixture to stand for 30 minutes, the boundary layer remained on the organic layer side, and phase separation was performed. The organic layer thus obtained was then concentrated under reduced pressure to form 47.76 g of 1-benzenesulfonyloxy-5-chloropentane (3:R 1 =H, R 2=H, X 1 =Cl). However, the liquid thus obtained is a suspension containing a large amount of solids, which appear to be precipitated salts of the reaction products, and therefore is filtered using a glass filter to form 1-benzenesulfonyloxy-5-chloropentane (3:R). 1 =H, R 2 =H, X 1 =Cl) (46.88 g, 0.16 mol, purity 92.91%), yield 82.89%.

[0207] Thus obtained 1-benzenesulfonyloxy-5-chloropentane (3: R 1 =H, R 2 =H, X 1 The polynomial spectral data of =Cl) are the same as those in Example 5.

[0208] Example 7: 1-Chloro-5-(p-Toluenesulfonyloxy)pentane (3:R 1 =H, R 2 =CH3, X 1 Preparation of Cl)

[0209]

[0210] A reaction similar to that in Example 5 was performed, but under the conditions that benzenesulfonyl chloride (35.32 g, 0.20 mol) was replaced with p-toluenesulfonyl chloride (38.13 g, 0.20 mol). The reaction mixture was transferred to a separatory funnel and allowed to stand, and the degree of separation between the organic and aqueous layers was checked after 1 minute and then after 30 minutes. Separation was good at 1 minute and 30 minutes. No boundary layer was observed. After allowing the reaction mixture to stand for 30 minutes, phase separation was performed, and the organic layer thus obtained was concentrated under reduced pressure to form 1-chloro-5-(p-toluenesulfonyloxy)pentane (3:R 1 =H, R 2 =CH3, X 1 =Cl)( 50.49 g, 0.17 mol, purity 92.16%), yield 84.06%. The 1-chloro-5-(p-toluenesulfonyloxy)pentane (3:R) thus obtained... 1 =H, R 2 =CH3, X 1 The concentrated solution of Cl) contains no solids or residues and the liquid is not cloudy.

[0211] The following is an example of 1-chloro-5-(p-toluenesulfonyloxy)pentane (3:R) thus obtained. 1 =H, R 2 =CH3, X 1 =Cl) spectral data.

[0212] Nuclear magnetic resonance spectroscopy: 1 H-NMR(500 MHz, CDCl3): δ=1.42-1.50(2H, m), 1.67(2H, tt, J=6.5 Hz, 6.5 Hz), 1.71(2H, tt, J=6.5 Hz, 6.5 Hz), 2.45(3H, s), 3.47(2H, t, J=6.5 Hz), 4.03(2H, t, J=6.5 Hz), 7.35(2H, d, J=8.4 Hz), 7.78(2H, d, J=8.4 Hz); 13 C-NMR (125 MHz, CDCl3): δ=21.60, 22.77, 28.10, 31.75, 44.51, 70.09, 127.83,129.82, 132.99, 144.77.

[0213] Mass spectrometry: EI-mass spectrometry (70 eV): m / z 276 (M + ), 173, 155, 121, 107, 91, 68.

[0214] Infrared absorption spectrum (D-ATR): ν=2956, 1598, 1456, 1359, 1177, 1098, 948, 816, 664, 555.

[0215] Example 8: 1-Chloro-5-(p-Toluenesulfonyloxy)pentane (3:R 1 =H, R 2 =CH3, X 1 Preparation of Cl)

[0216]

[0217] The reaction mixture was prepared in the same manner as in Example 7, including scale, until the reaction was completed in 9 hours. A brine solution (prepared from sodium chloride (25.30 g) and water (80.00 g)) was then added to the reaction mixture, followed by tetrahydropyran (20.00 g), and the reaction mixture was stirred for 30 minutes. After stirring, the reaction mixture was transferred to a separatory funnel. Specifically, unlike in Example 7, methanol (20.00 g) was not added. The reaction mixture was allowed to stand, and the degree of separation between the organic and aqueous layers was verified after 1 minute and then after 30 minutes. At 1 minute and 30 minutes, the separation was unsatisfactory, and a turbid boundary layer remained. After allowing the reaction mixture to stand for 30 minutes, the boundary layer remained on the organic layer side, and phase separation was performed. The organic layer thus obtained was then concentrated under reduced pressure to form 52.73 g of 1-chloro-5-(p-toluenesulfonyloxy)pentane (3:R 1 =H, R 2 =CH3, X 1 =Cl). However, the liquid thus obtained is a suspension containing a large amount of solids, which appear to be precipitated salts of the reaction products, and therefore is filtered using a glass filter to form 1-chloro-5-(p-toluenesulfonyloxy)pentane (3:R). 1 =H, R 2 =CH3, X 1 =Cl) (50.03 g, 0.17 mol, purity 93.22%), yield 84.25%.

[0218] Thus obtained 1-chloro-5-(p-toluenesulfonyloxy)pentane (3:R 1 =H, R 2 =CH3, X 1 The polynomial spectral data of =Cl) are the same as those in Example 7.

[0219] Example 9: 1-Chloro-3,7,11-Trimethyldodecane (5:X) 1 Preparation of Cl)

[0220]

[0221] At room temperature, magnesium (32.89 g, 1.35 g atom) and tetrahydrofuran (386.70 g) were placed in a reactor and stirred at 60 to 65 °C for 11 minutes. Then, at 60 to 75 °C, 1-chloro-2,6-dimethylheptane (10:X) was added... 2 =Cl)(209.75 g, 1.29 mol, 100% purity) was added dropwise to the reactor. After the addition was complete, the reaction mixture was stirred at 75 to 80 °C for 3 hours to form 2,6-dimethylheptylmagnesium chloride (4:M 1 =MgCl).

[0222] Next, copper chloride (0.81 g, 0.0064 mol), lithium chloride (0.51 g, 0.013 mol), tetrahydrofuran (400.00 g), and 1-benzenesulfonyloxy-5-chloro-3-methylpentane (3:R) prepared as in Example 1 were added. 1 = CH3, R 2 =H, X 1 = Cl) (375.23 g, 1.22 mol, purity 84.09%) was placed in another reactor, and then the above-mentioned 2,6-dimethylheptylmagnesium chloride (4: M) was added dropwise to another reactor at 20 to 30 °C. 1 = MgCl). After the addition was complete, the reaction mixture was stirred at 20 to 30°C for 3 hours. Then methanol (187.50 g) and water (86.67 g) were added to the reaction mixture, followed by phase separation. The resulting organic layer was concentrated under reduced pressure, and the concentrate was then distilled under reduced pressure to form 1-chloro-3,7,11-trimethyldodecane (5:X). 1 =Cl) (249.64 g, 0.96 mol, purity 96.17%, bp = 128.4 to 131.1℃ / 0.12 kPa (0.92 mmHg)), yield 78.78%.

[0223] The following is an example of how 1-chloro-3,7,11-trimethyldodecane (5:X) was obtained. 1 =Cl) spectral data.

[0224] Nuclear magnetic resonance spectroscopy: 1 H-NMR (500 MHz, CDCl3): δ=0.83-0.91(12H, m), 1.02-1.42(13H, m), 1.48-1.69(3H, m), 1.75-1.84(1H, m), 3.50-3.62(2H, m); 13 C-NMR(125MHz, CDCl3): δ=19.05, 19.12, 19.66, 19.72, 22.61, 22.71, 24.23, 24.79, 24.81,27.97, 30.38, 30.41, 32.74, 32.76, 36.90, 36.96, 37.23, 37.25, 37.28, 37.36,39.35, 39.77, 39.85, 43.37.

[0225] Mass spectrometry: EI-mass spectrometry (70 eV): m / z 246 (M+ ), 231, 203, 175, 161, 147, 133, 113, 97, 83, 71, 57, 43.

[0226] Infrared absorption spectrum (D-ATR): ν=2955, 2926, 1463, 1379, 730, 660.

[0227] Example 10: Preparation of 6,10,14-trimethyl-2-pentadecanol (8)

[0228]

[0229] At room temperature, magnesium (30.34 g, 1.25 g atom) and tetrahydrofuran (356.70 g) were placed in a reactor and stirred at 60 to 65 °C for 22 minutes. Next, at 60 to 75 °C, 1-chloro-3,7,11-trimethyldodecane (5:X) prepared as in Example 9 was added. 1 =Cl) (307.68 g, 1.19 mol, purity 96.17%) was added dropwise to the reactor. After the addition was complete, the reaction mixture was stirred at 75 to 80 °C for 2.5 hours to form 3,7,11-trimethyldodecyl magnesium chloride (6:M 2 =MgCl).

[0230] The internal temperature of the reactor was then cooled to 1 to 10 °C, and cuprous chloride (0.25 g, 0.0024 mol, 95% purity) was added to the reactor, followed by the dropwise addition of propylene oxide (79.42 g, 1.36 mol) at 5 to 30 °C. After the addition was complete, the reaction mixture was stirred at 15 to 25 °C for 2 hours. An aqueous solution of acetic acid (prepared from acetic acid (162.26 g) and water (327.59 g)) was then added to the reaction mixture, followed by phase separation. The resulting organic layer was then concentrated under reduced pressure, and the concentrate was distilled under reduced pressure to form 6,10,14-trimethyl-2-pentadecanol (8) (288.54 g, 1.06 mol, 99.56% purity, bp = 145.0 to 153.1 °C / 0.12 kPa (0.90 mmHg)), in 89.33% yield.

[0231] The following are the spectral data of 6,10,14-trimethyl-2-pentadecanol (8) obtained in this way.

[0232] Nuclear magnetic resonance spectroscopy: 1H-NMR(500 MHz, CDCl3): δ=0.85(12H, dt, J=6.1 Hz, 6.1 Hz),1.00-1.16(6H, m), 1.18(3H, d, J=6.1 Hz), 1.20-1.47(15H, m), 1.52(1H, dq, J=6.5 Hz, 6.5 Hz), 3.79(1H, sext-like, J=6.1 Hz); 13 C-NMR (125 MHz, CDCl3): δ=19.60, 19.67, 19.73, 22.61, 22.70, 23.21, 23.23, 23.25, 23.47, 23.51, 24.45,24.78, 24.80, 27.96, 32.72, 32.75, 32.78, 36.99, 37.02, 37.08, 37.11, 37.27,37.30, 37.32, 37.37, 37.42, 39.35, 39.69, 39.71, 68.17, 68.21.

[0233] Mass spectrometry: EI-mass spectrometry (70 eV): m / z 269 (M + -1), 252, 224, 182, 167, 140, 126,111, 97, 71, 57, 43.

[0234] Infrared absorption spectrum (D-ATR): ν=3330, 2954, 2926, 1463, 1377, 1121, 938.

Claims

1. A method for preparing 1-arylsulfonyloxy-5-haloalkane compounds of the following general formula (3): Where R 1 and R 2 Each can independently represent a hydrogen atom or a methyl group, and X 1 Represents halogen atoms, The method includes the following steps: Tetrahydropyran compounds of the following general formula (1): Where R 1 Indicates a hydrogen atom or a methyl group. Ring-opening reaction with aryl sulfonyl halide compounds of general formula (2) in the presence of zinc chloride: Where R 2 Represents a hydrogen atom or a methyl group, and X 1 Represents halogen atoms, To form the above-mentioned 1-aransulfonyloxy-5-haloalkane compound (3).

2. A method for preparing 1-halo-3,7,11-trimethyldodecane compounds of the following general formula (5): Where X 1 Represents halogen atoms, The method includes the following steps: According to the method of claim 1, from tetrahydropyran compound (1), wherein R 1 =CH3, to prepare 1-arylsulfonyloxy-5-haloalkane compound (3), wherein R 1 =CH3, i.e., 1-arylsulfonyloxy-5-haloalkyl compound (3: R 1 =CH3), and Make the nucleophile 2,6-dimethylheptyl compound of the following general formula (4): Where M 1 Indicates Li, Mg, Z 1 CuZ 1 or CuLiZ 1 And Z 1 This indicates a halogen atom or a 2,6-dimethylheptyl group. With 1-arylsulfonyloxy-5-halo-3-methylpentane compounds (3: R 1 =CH3) undergoes a coupling reaction to form the above-mentioned 1-halo-3,7,11-trimethyldodecane compound (5).

3. A method for preparing 6,10,14-trimethyl-2-pentadecanol of the following general formula (8): The method includes the following steps: According to the method of claim 1, from tetrahydropyran compound (1), wherein R 1 =CH3, to prepare 1-arylsulfonyloxy-5-haloalkane compound (3), wherein R 1 =CH3, i.e., 1-arylsulfonyloxy-5-haloalkyl compound (3: R 1 =CH3), Make the nucleophile 2,6-dimethylheptyl compound of the following general formula (4): Where M 1 Indicates Li, Mg, Z 1 CuZ 1 or CuLiZ 1 And Z 1 This indicates a halogen atom or a 2,6-dimethylheptyl group. With 1-arylsulfonyloxy-5-halo-3-methylpentane compounds (3: R 1 =CH3) undergoes a coupling reaction to form a 1-halo-3,7,11-trimethyldodecane compound of the following general formula (5): Where X 1 Represents halogen atoms, The 1-halo-3,7,11-trimethyldodecane compound (5) thus obtained is converted into a nucleophilic 3,7,11-trimethyldodecane compound of the following general formula (6): Where M 2 Indicates Li, Mg, Z 2 CuZ 2 or CuLiZ 2 And Z 2 Indicates a halogen atom or 3,7,11-trimethyldodecyl. as well as The nucleophile 3,7,11-trimethyldodecyl compound (6) thus obtained was subjected to a nucleophilic addition reaction with propylene oxide of the following formula (7): To form the above-mentioned 6,10,14-trimethyl-2-pentadecanol (8).

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