JPH02129136A - Optically active compound and production thereof - Google Patents

Abstract

NEW MATERIAL:An optically active compound expressed by formula I [A is chemically active substitutent group; m and n are integer of 0-18 (either one is 0 or 1 and m+n>=1); X is single bond, CO or COO; B is H, 1-18C alkyl, benzyl or tetrahydropyranyl capable of having substitutent group (halogen or alkoxy); * represents optical active]. EXAMPLE:An optically active 4-benzyloxy-1-trifluoromethylbutyl alcohol. USE:An optically active intermediate, especially useful as an intermediate for various kind of liquid crystal compounds as well as useful as intermediate for medicine, insecticide, agricultural chemical, etc., and capable of readily changing the structure. PREPARATION:Either one optical isomer of compound expressed by formula II (Z is H or B except tetrahydropyranyl; k is integer of 3-18; D is alkyl or phenyl) is selectively hydrolyzed with a lipase to provide the optically active compound expressed by formula III in formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel optically active compound and a method for producing it. More specifically, the present invention relates to optically active compounds useful as intermediates for producing various liquid crystal compounds and production methods.

[Prior Art] Conventionally, various ferroelectric liquid crystals have been used as liquid crystal compounds, such as p-n-decyloxybenzoic acid-p'-(2-methylbutyloxy)phenyl ester and p-n-nonyloxybenzoic acid-p' -(4-Methylhebutyloxycarbonyl)phenyl ester is known [Journal of the American Chemical Society]
10
8. 4738°1911fi], 2-methylbutanol and 4 as intermediate optically active compounds, respectively.
-Methylhexanol is used. Other known optically active intermediates include chain hydrocarbon derivatives, amino acid derivatives, and cholesterol derivatives.

[Problems to be solved by the invention] However, it is generally difficult to change the structure of these optically active intermediates (chain hydrocarbon derivatives, cholesterol derivatives, etc.), and when they are made into derivatives such as liquid crystal compounds, the properties of these optically active intermediates are difficult to change. Prone to have adverse effects (amino acid derivatives, cholesterol derivatives, etc.), very expensive (chain hydrocarbon derivatives, etc.)
, etc.

[Means for Solving the Problems] As a result of intensive studies aimed at obtaining an optically active substance whose structure can be easily changed and which is useful as an optically active intermediate, the present inventors have developed the present invention. reached.

That is, the present invention is based on the general formula [wherein A is a chemically active substituent, ffhn is each an integer from 0 to 1B, and one of rl'h n is O or! and satisfies the relationship m+n≧1. X is a single bond, -CO- or -COO-,
B is a hydrogen atom; an alkyl group having 1 to 18 carbon atoms which may be substituted with a halogen atom or an alkoxy group; a benzyl group or a tetrahydropyranyl group; * indicates optical activity. ] An optically active compound represented by. and general formula c, where Z is a benzyl group; an alkyl group having 1 to 18 carbon atoms which may be substituted with a halogen atom or an alkoxy group, k is an integer of 3 to 18, and D is an alkyl group or Represents a phenyl group. A general formula characterized by selectively hydrolyzing one optical isomer of the ester derivative represented by [wherein Z is a benzyl group; A few f~! 8 alkyl group, k is an integer from 3 to 18, and the wooden stamp indicates optical activity. ] This is a method for producing an optically active alcohol.

In general formula (1), the chemically active substituent of A includes a hydroxyl group, a halogen atom, a benzyloxy group, a tosyloxy group, a p-benzyloxyphenyloxy group, a tetrahydropyranyl group, and the like.

B is an alkyl group having 1 to 18 carbon atoms which may be substituted with a halogen atom or an alkoxy group, and straight-chain alkyl groups (methyl, ethyl, propyl, butyl,
Pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, octadecyl group, etc.), branched alkyl group (isopropyl group, I- Methylpropyl group, l-methylbutyl group, I-methylhexyl group, !-methylheptyl group,
2-methylbutyl group, 2-methylpentyl group, 2-methylhexyl group, 2-methylheptyl group, 2-methyloctyl group, 3-methylpentyl group, 4-methylpentyl group, 4-methylhexyl group, 5-methyl heptyl group, B-
methyloctyl group, 7-methylnonyl group, 8-methyldecyl group, 3-methyldecyl group, etc.), alkyl groups that grow substituents [for example, rI! with CI (chlorine atom)! substituted alkyl groups (2-chloropropyl group, 2-chlorobutyl group, 2-chloropentyl group, 2-chlorohexyl group,
-Chloroheptyl group, 2-chlorooctyl group,! -chloro-2-methylpropyl L l-chloro-2-methylbutyl group, l-chloro-3-methylbutyl group, etc.),
Alkyl group substituted with F (2-fluoropropyl group,
2-fluorobutyl group, 2-fluoropentyl group, 2-
(fluorohexyl group, 2-fluoroheptyl group, 2-fluorooctyl group, 1-fluoro-2-methylpropyl group, 1-fluoro-2-methylbutyl group, 1-fluoro-3-methylbutyl group, etc.), alkyloxy group Substituted alkyl groups (2-methoxypropyl group, 2-ethoxypropyl group, 2-propyloxypropyl group, 3-
Methoxybutyl group, 3-ethoxybutyl group, 3-propyloxybutyl group, 4-methoxypentyl group, 4-ethoxypentyl group, 4-propyloxypentyl group, 3-
methoxypropyl group, 3-ethoxypropyl group, 3-propyloxypropyl group, 3-hexyloxypropyl group, 4-methyloxybutyl group, 4-propyloxybutyl group, 4-hexyloxybutyl group, etc.) optically active alkyl group (optically active 2-methylbutyl group, optically active 2-methylpentyl group, optically active 2-methylhexyl group, optically active 2-methylheptyl group, optically active 2-
Methyloctyl group, optically active 3-methylpentyl group, optically active 4-methylhexyl group, optically active 5-methylheptyl group, optically active 6-methyloctyl group, optically active! −
methylpropyl group, optically active 1-methylbutyl group, optically active I-methylheptyl group, optically active 1-methyloctyl group, etc.) and optically active alkyl groups having 14 substituents [e.g. Optically active alkyl group (optically active 2-chloropropyl group, optically active 2-chlorobutyl group, optically active 2-chloropentyl group,
Optically active 2-chlorohexyl group, optically active 2-chloroheptyl group, optically active 2-chlorooctyl group, optically active l
-chloro-2-methylpropyl group, optically active l-chloro-2-methylbutyl group, optically active l-chloro-3-methylbutyl group), optically active alkyl group substituted with F (fluorine atom) (optically active 2-fluoropropyl group,
Optically active 2-fluorobutyl group, optically active 2-fluoropentyl group, optically active 2-7/L/ohexyl group, optically active 2-fluoroheptyl group, optically active 2-fluorooctyl group, optically active 1-fluoro -2-methylpropyl group, optically active 1-fluoro-2-methylbutyl group, optically active! -fluoro-3-methylbutyl group) and optically active alkyl groups substituted with alkyloxy groups (optically active 2-methoxypropyl group, optically active 2-ethoxypropyl group, optically active 2-propyloxypropyl group, optically active 2-butyloxypropyl group, optically active 2-hexyloxypropyl group, optically active 3-methoxybutyl group, optically active 3-ethoxybutyl group, optically active 3
-Propyloxybutyl group, optically active 4-methoxypentyl group, optically active 4-ethoxypentyl group, optically active 4
-propyloxypentyl group, optically active 4-butyloxypentyl group, optically active 4-hexyloxypentyl group, optically active 4-(2-methylbutyloxy)butyl group,
Optically active 2-ethyloxy-3,3,3-)lifluoropropyl group, optically active l-methyloxy-4,4,4-
) Lifluorobutyl group, optically active 4-ethyloxy-5
,5,5-)lifluorohentyl group, optically active 5-ethyl-o+'y-G,G, [i-trifluorohexyl group, optically active B-ethyloxy-7,7,7-)lifluoroheptyl group , optically active ■-methyloxyethyl group,
Optically active 1-ethyloxyethyl group, optically active! -Propyloxyethyl group, optically active I-butyloxyethyl group, optically active! -Hexyloxyethyl group, optically active!
-methyloxy-2,2,2-)lifluoroethyl group,
Optically active 1-ethyloxy-2,2,2-)lifluoroethyl group, optically active! -propyloxy-2,2,2-
Trifluoroethyl group, optically active! -butyloxy-2
,2,2-)lifluoroethyl group, optically active 1-hexyloxy-2,2,2-)lifluoroethyl group, optically active l-methyl-2-methyloxyethyl group, optically active!
-Methyl-2-ethyloxyethyl group, optically active 1-methyl-2-propyloxyethyl group, optically active 1-methyl-2-butyloxyethyl group, optically active 1-methyl-
2-hexyloxyethyl group, optically active! -Methyl-3
-Methyloxypropyl group, optically active 1-methyl-3-
Ethyloxypropyl group, optically active l-methyl-3-butyloxypropyl group, optically active! -Methyl-4-methyloxybutyl group, optically active 1-methyl-4-ethyloxybutyl group, optically active l-methyl-4-butyloxybutyl group, optically active! -Methyl-5-methyloxypentyl group, optically active! -Methyl-5-ethyloxypentyl group, optically active 1-methyl-5-butyl-oxyheptyl group, optically active 1-methyl-7-methyloxyheptyl group, optically active 1-methyl-7-nityloxyheptyl group,
Optically active 1-methyl-7-butyloxyheptyl group, optically active 1-)lifluoromethyl-2-ethyloxyethyl group, optically active 1-)lifluoromethyl-3-ethyloxypropyl group, optically active 1-tri Fluoromethyl-4
-ethyloxybutyl group, optically active I-trifluoromethyl-5-ethyloxypentyl group, optically active 1-)lifluoromethyl-7-nityloxyhebutyl group, etc.)
etc.].

Among these, preferably an alkyl group having 1 to 9 carbon atoms.

Specific examples of the optically active compound represented by the general formula (1) include compounds having groups and numbers as shown in Table 1.

Margin table below this page - 1 (1) Table - 1 (2) Table ■ 衷衷衷衷表 衷表衷表 (1 cow) Mug (1q) 衷表表 (1ri) 衷Muoni (supplement) The margins below this page Optically active alcohol represented by general formula (3) [- general formula (
3) Compound and abbreviation. The same description will be used below. Ko is
It can be produced by biochemically selectively hydrolyzing one optical isomer of the compound of general formula (2) using lipase.

In general formulas (2) and (3), the alkyl group having 1 to 18 carbon atoms which may be substituted with a halogen atom or alkoxy group in Z is substituted with a halogen atom or alkoxy group in B in general formula (1). Number of carbon atoms that may be 1 or more
It is the same as the alkyl group in No. 18.

The alkyl group or phenyl group of D is a straight chain argyl group (methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, Te). labucyl group, etc.),
Branched alkyl groups (isopropyl group, 2-methylpropyl group, 3-methylbutyl group, 1-methylpentyl group, 2p
'L4-trimethylpentyl group, etc.) and phenyl groups can be used; however, alkyl groups having 4 or more carbon atoms and phenyl groups are preferable, since products and unreacted substances can be separated by vacuum distillation.

1 to 1 lipase per mole of the compound of general formula (2)
, 000.000.000 units [The unit refers to the enzyme unit that indicates the ability to digest fat, Yamada et al.
p., 860-864.1962) at a rate of 11. The amount of enzyme that releases t moles of fatty acids is defined as one unit. ], preferably 100 to 5oo, ooo, ooo
Use units.

The reaction is usually carried out by adding lipase to water, then adding the compound of general formula (2) and stirring.

The reaction temperature is usually 20-60°C, preferably 35-55°C.
It is °C. 1) tI is usually 3.0 to 8.0, preferably 6.0 to 7.0, and can be adjusted as necessary by adding an aqueous solution of an alkali metal hydroxide such as sodium hydroxide. Can be done. The end point of the reaction varies depending on the compound of general formula (2) that is the substrate, but usually the hydrolysis rate is 5.
~50%, preferably 20 to 49%, and the progress of the reaction is usually monitored using a gas chromatography column, etc., and the reaction is terminated by cooling to 20°C as soon as a predetermined hydrolysis rate is reached. be able to. After the reaction, the compound of general formula (3) and the unreacted general formula (2) are purified by methods such as ether extraction, vacuum distillation, and column separation.
The compound is released by rF. The halved compound (alcohol) of general formula (3) is one of a pair of optical isomers,
The other optically active alcohol can be obtained by hydrolyzing the unreacted compound of general formula (2). General formula (3)
The compound can be confirmed by IR spectrum, NMR spectrum, etc.

The compound of general formula (1) can be synthesized, for example, through the following steps. (In the following formula, A, , Bz represents a benzyl group, Ts represents a tosyl group, J
indicates an iodine atom. ) (1) When m is 3 to 18 and n is 0, 82-Hat.

↓　　　HO-(CH2)p-OH Bz-0-(CH2)p-0)1 ↓　　　　　　Ha0y-shi conversion Bz-0-(CH2)p-Hal.

↓ Mg ↓ CIl'3-Coo-C2H3Bz
-0-(CH2)p-CO-CF3
(5) ↓ NaBH/l or LiAlH4 ↓ Hal, -CD-D ↓ Rehabilitation 0-t゛ is ○+HCIaq.

↓ I'd/C+ 82 ↓ NaB)lto or LiAl)14 Naoriz-0-Q-OH ↓ )fal, -(C)12)p-)1a
l.

B2-0-Ω-0-(CH2)p-Hal-(6) to synthesize the compound of general formula (6), and synthesize the compound of general formula (6) with the general formula (
React in the same way as compound 4)! - can.

(2) When m is 0 and n is 3 to 18, Hal, -11, or ○ ↓ No-(CH2)ρ-0H HO-(C112)p-0-[3 ↓ ))n Cane stopper Hat , -(CH2)p-0-8 ↓ CF3-Coo-C2) f5CF3
-CO-(C)12)ρ-0-8↓ D-CO-)1a l.

↓ Reha 0-Se'' In addition, the compound of general formula (7) can also be synthesized by the following route using the compound of general formula (5).

[? z-0-(CI2)p-CO-CF3
(5) ↓ Pd/C182 )to-(CH2)p-Co-CF3 ↓ Ag2O" J4t NaH" ) fat
−8+ or ○+HCIaq.

CF3-C0-(CH2)ρ-0-G
(7) (3) When m is O and n is 1 to 18, F3 HO-C:I:H-(CH2)q-COO-R(8)↓
Ag2O+ Bz-J, or Na)t +
Bz-Hal.

↓ LiAI) 14 ↓ 5-CI ↓ CH2(Coo-C2H5>2 ↓ aOH ↓ ↓ and ↓ ↓ ↓ C02 1AIH4 Ho-canizing agent g and ↓ Pd/C+ 82 ↓ l-1cHO General formula (10) compound of By the synthetic operation of the compounds of general formula (11) and general formula (13), optically active fluors having carbon chains extended by 2 and 1, respectively, are obtained, and by repeating this operation, the following compounds are obtained.

Moreover, using the compound of general formula (8) ↓ ○ + HCIaq.

Hereinafter, by obtaining and reacting the compound of general formula (14) in the same manner as the compound of general formula (9), the following compound is obtained.

is ○+HCIaq.

B2-〇-Tan・1(-(CH2).-〇-X-[3 or less, (i'F3 TIP-0-(JH-(CI+2)n-Off↓ Acid catalyst compound of general formula (15) The following compound can be obtained by performing the same operation as that used to synthesize the compounds of general formula (11) and general formula (13) from the compound of general formula (10).

(i'F3 HQ-(C)t2)m-C:CH-Q-Bm is 1 to 18
, when n is 1, (4) when m is 1 to 18, and n is 0, ↓ LiAI) 14 ↓ LiAl) 14 Using the compound of general formula (17), from the compound of general formula (10) The following compound can be obtained by performing the same operations as those for synthesizing the compounds of formula (11) and general formula (13).

m is 11 When n is 1 to 18, ↓ ↓ aH +Bz-Hal- 1AIH4 ↓ is○+)lcIaq.

Pd/C+ )+2 Using the compound of general formula (10), the following operations were performed in the same manner as for synthesizing the compounds of general formula (11) and general formula (13) from the compound of general formula (10). A compound is obtained.

below Also, using the compound of general formula (16) ↓ ○ + Soup C1aq.

The following compound is obtained by reacting the compound of general formula (21) in the same manner as the compound of general formula (18).

can be used to produce a liquid crystal compound shown below, which exhibits the following phase transition.

↓ Acid catalyst In addition, the liquid crystal compound represented by formula (23) is the compound of the present invention (
24), for example, by the following route.

↓ 5-CI The compound of the present invention can be used as an intermediate raw material for liquid crystal compounds. For example, the compound of the present invention may be used as a compound of the present invention [Example 2] The present invention will be further explained with reference to Examples below, but the present invention is not limited thereto.

In the following explanation, the specific optical rotation is subject to slight variations depending on the measurement method and purity.

Example 1 Production of optically active 4-benzyloxy-1-trifluoromethylbutyl alcohol (Compound No. 59 in Table 1) (1) Production of 3-benzyloxypropyl alcohol Dissolve 218 g of KOH in 828 g of trimethylene glycol. After that, 218 g of benzyl chloride was added dropwise over about 1 hour. After reacting at 130°C for 2 hours, it was added to 1500 ml of water, washed with water, and then distilled under reduced pressure to obtain 481 g of 3-benzyloxypropyl alcohol (b, p, 1
25-+27°C/limmHg).

(2) Production of 3-benzyloxytochloropropane After dissolving 324 g of 3-benzyloxypropyl alcohol in 1200 ml of carbon tetrachloride, 809 g of triphenylphosphine was added and the mixture was reacted at room temperature for 2 days. After filtering off the precipitate, vacuum distillation was performed to obtain 292 g of 3-benzyloxy-1 chloropropane (b, p, 110 to IIG°C
15mmHg).

(3) Production of 3-benzyloxypropyl-trifluoromethylketone Dissolve 97.4 g of trifluoroacetic acid ethyl ester in 500 ml of dry ethyl ether, cool to below -30°C, and cool to 3-benzyloxy-1-chloropropane. 12
A solution of 700 ml of dry ethyl ether of a Grignard reagent synthesized from 7 g and 7 g of M g I[i] was added dropwise.

After stirring at 30"C, the temperature was returned to room temperature and 50 ml of water was added. After removing ethyl ether under reduced pressure, vacuum distillation was performed to obtain 113.7 g of 3-benzyloxypropyl-trifluoromethyl ketone (b ,1) ,108
~! 10℃/! 2mmHg).

(4) Lithium aluminum hydride I [i. After adding fig, 3-benzyloxypropyl-trifluoromethylketone 53 was added under water-cooling conditions.
, 8 g of dry ethyl ether in 200 ml was added dropwise. After removing the precipitate and removing ethyl ether under reduced pressure, vacuum distillation was performed to obtain 49.8 g of 4-benzyloxy-1)rifluoromethylbutyl alcohol (+33
°C15mmHg).

(5) Production of 4-benzyloxy-1-trifluoromethylbutyl-benzoate 31.9 g of 4-benzyloxy-1-trifluoromethylbutyl alcohol and 20.3 g of dry pyridine
was dissolved in 90 ml of dry toluene, and then a solution of 25.3 g of benzoylchloroljl' in 50 ml of dry toluene was added dropwise at room temperature. After reacting at room temperature for 10 hours, the reaction mixture was washed with 6N hydrochloric acid, dilute KOH aqueous solution, and water in this order. After removing toluene under reduced pressure, vacuum distillation was performed to obtain 37.8 g of 4-benzyloxy-l trifluoromethylbutyl-benzoate (b, 1), 160°C, 10.4 mmHg).

(6) Production of optically active 4-benzyloxy-1-)lifluoromethylbutyl alcohol Add 1200 ml of water to a jar fermenter and heat to 40°C, then add lipase (Lipase MY, manufactured by Meito Sangyo Co., Ltd.).
130,000 units/g) was added and stirred for 30 minutes. 43.8 g of 4-penzyloxo-1-trifluoromethylbutyl-benzoate was added to this, and the reaction system was heated to a water temperature of 40'' C1 pH 6.4 ~ B.B, if
The progress of hydrolysis was checked by gas chromatography while maintaining the pumping speed at 500 ml), and after about 8 hours (hydrolysis rate: 45%), the mixture was cooled to 10°C. After extraction with 700 ml of ethyl ether, vacuum distillation was performed to obtain 13.0 g of optically active 4-benzyloxy-1-trifluoromethylbutyl alcohol, which is the compound of the present invention.

b. p. ;92 ~9[i℃10.25mmHg
Optical purity: 90.4% e (measured by F-NMR and capillary gas chromatography after treatment with MTPA-C I) Example 2 Optically active 4-benzyloxy-1-)lifluoromethylbutyl-ethyl ether (Table 1, No. 189)
Compound) 9.85 g of the optically active 4-benzyloxy-1-trifluoromethylbutyl alcohol prepared in Example 1 and 25 g of silver oxide were added to 52.8 ml of ethyl iodide, and the mixture was stirred at room temperature for 3 days. Suction school! Insoluble materials were removed by filtration. Ethyl iodide was removed under reduced pressure to obtain optically active 4-benzyloxy-1-trifluoromethylbutyl-ethyl ether lOJg, which is a compound of the present invention.

IR(am-'); 2930,1450.138
0.1275.1120 Compound optically active 4-ethyloxy-5,5,5-)lifluoropentyl alcohol 1), p, ; 81-b I R (am-'): 3370.2940,12
75.1180.1125!9 The H-NMR spectrum and F-NMR spectrum of this compound are shown in FIG. 1 and FIG. 2, respectively.

Example 3 Production of optically active 4-ethyloxy-5,5.5-)rifluoropentyl alcohol (Table 1, compound No. 18) Optically active 4-benzyloxy-5,5.5-) produced in Example m@2 Lifluoromethylbutyl-ethyl ether 7,
After dissolving 5 g in 136 ml of ethanol, debenzylation was performed using 2.0 g of 5% Pd/C (palladium on carbon) in a hydrogen atmosphere. [Effects of the Invention] The present invention provides a novel optically active compound and a manufacturing method,
Furthermore, these novel optically active compounds and production methods have the following remarkable characteristics.

(1) It is an optically active compound having a structure in which a CF3 group with large polarization is directly connected to a chiral carbon, and is extremely effective as an intermediate for synthesizing various liquid crystal compounds.

Due to this large polarization on chiral carbon, a large spontaneous polarization value is expected when it is made into a liquid crystal compound.

(2) The structure can be easily changed, and optically active compounds with various structures are provided. By this means, for example, when a liquid crystal compound is introduced, it is possible to control physical properties and performance such as the type of liquid crystal phase, phase transition temperature, optical anisotropy, and dielectric anisotropy.

(3) Because it has a chemically active substituent, its uses are not limited to intermediates for liquid crystal synthesis, but are extremely useful as intermediates for the synthesis of various physiologically active compounds such as pharmaceuticals, insecticides, and agricultural chemicals.

(4) In addition to its use as a synthetic intermediate, a liquid crystal composition that can be used as a ferroelectric liquid crystal can be obtained by blending the optically active compound of the present invention with a smectic liquid crystal that itself does not have any optically active sites. can.

(5) In addition to its use as a hardening intermediate, by blending the optically active compound of the present invention with nematic liquid crystal,
This has the effect of suppressing the occurrence of reverse domains in TN type liquid crystal cells.

(6) This is a method for producing optically active alcohols with high yield in a small number of steps by using an inexpensive ester as a raw material and using optical isomer-selective hydrolysis using lipase.

[Brief explanation of drawings]

FIG. 1 shows the H-NMR spectrum of the compound obtained in Example 3, and FIG. 2 shows the F-NMR spectrum of the same compound.

Claims (1)

[Claims] 1. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) [In the formula, A is a chemically active substituent, and m and n are each an integer of 0 to 18. , and one of m and n is 0 or 1, and the relationship m+n≧1 is satisfied. X is
A single bond, -CO- or -COO-, B is a hydrogen atom; an alkyl group having 1 to 18 carbon atoms which may be substituted with a halogen atom or an alkoxy group; a benzyl group or a tetrahydropyranyl group, * The mark indicates optical activity. ] An optically active compound represented by. 2. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (2) [In the formula, Z is a benzyl group; an alkyl group having 1 to 18 carbon atoms that may be substituted with a halogen atom or an alkoxy group, and k is an integer from 3 to 18, and D represents an alkyl group or a phenyl group. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (3) [In the formula, Z is a benzyl group; It is an alkyl group having 1 to 18 carbon atoms which may be substituted with a halogen atom or an alkoxy group, k is an integer of 3 to 18, and the mark * indicates optical activity. ] A method for producing an optically active alcohol.