JP2555129B2 - Optical resolution of (±) -1-para-substituted phenylethanol - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial application] The present invention relates to a method for optical resolution of (±) -1-para-substituted phenylethanol.

[Prior Art] Conventionally, as a report on an optical resolution method of 1-para-substituted phenylethanol, fatty acid ester of 1-para-substituted phenylethanol was obtained by using crushed liver of pig, cow, rat, horse, sheep, dog, etc. Asymmetrically hydrolyzing agar in an aqueous solution (hereinafter referred to as asymmetric hydrolysis) (see JP-A-60-224494) and a method of asymmetrically reducing parahaloacetophenone with yeast (tetrahedron letters ( Tetrahedron letter
s), vol. 25, pp. 3979-3982 (1984)).

However, in the method (1), the reaction is carried out in an aqueous system, and therefore a derivative having a branched chain in which the alkyl group as the substituent of the phenyl group of the starting material 1-para-substituted phenylethanol derivative has 4 or less carbon atoms is reported. However, in the case of a long-chain alkyl group having 5 or more carbon atoms,
It has a drawback that its dispersibility in water is remarkably reduced and asymmetric hydrolysis cannot be carried out. In addition, the method also has a drawback that it is difficult to apply to a derivative having an alkyl group, which is a substituent of a phenyl group, having 5 or more carbon atoms because it is an aqueous reaction, and also requires a large amount of yeast. Therefore, it is disadvantageous in terms of production equipment and production cost.

[Problems to be Solved by the Invention] In order to solve the problems that the present invention cannot be applied to the conventional ones having low solubility in water, and cannot be said to be a simple and economical method. It was made.

[Means for Solving the Problems] The present invention provides a compound of the general formula (I): (Wherein A represents a linear alkyl group having 1 to 10 carbon atoms or a linear alkoxy group having 1 to 12 carbon atoms) represented by (±) -1-para-substituted phenylethanol and trichloroethylbutyrate as esterases. An enzyme having activity is allowed to act on the (+) form of the compound represented by the general formula (I) to give the general formula (II): (In the formula, A is the same as above), and then a (+)-1-para-substituted phenylethanolbutyric acid ester is formed, and then the compound represented by the general formula (II) and the general formula (III): (In the formula, A is the same as above) and (-)-1-para-substituted phenyl ethanol are separated.

Examples In the present invention, general formula (I): (±) -1-para-substituted phenylethanol represented by the formula (A represents a linear alkyl group having 1 to 10 carbon atoms or a linear alkoxy group having 1 to 12 carbon atoms) is used.

A in the general formula (I) is a linear alkyl group having 1 to 10 carbon atoms or a linear alkoxy group having 1 to 12 carbon atoms as described above, and when the alkyl group or alkoxy group is not linear The compounds derived from these as synthetic raw materials are difficult to use in the fields of medicine, agricultural chemicals, liquid crystals and the like, and when the alkyl group or alkoxy group is out of the above range of carbon number, the It is not preferable because the synthetic yield of the compound represented by the general formula (I) as a raw material for resolution tends to be low.

Among the linear alkyl groups having 1 to 10 carbon atoms, those having 3 to 8 carbon atoms, and those having 1 to 12 carbon atoms in the linear alkoxy group having 3 to 10 carbon atoms, It is highly useful in fields such as agricultural chemicals and liquid crystals, especially in the field of liquid crystals, and further, the synthetic yield of the compound represented by the general formula (I) is good.

Specific examples of the compound represented by the general formula (I) having a linear alkyl group or a linear alkoxy group include (±) -1-paramethylphenylethanol and (±).
-1-para-butylphenylethanol, (±) -1-parapentylphenylethanol, (±) -1-paraoctylphenylethanol, (±) -1-paramethoxyphenylethanol, (±) -1-parapentyloxy Examples thereof include phenylethanol, (±) -1-parabutyloxyphenylethanol, (±) -1-paradecaneoxyphenylethanol, (±) -1-paralauryloxyphenylethanol.

The method for obtaining the compound represented by the general formula (I) is not particularly limited, and any method may be used as long as the compound can be obtained. For example, when the substituent A in the general formula (I) is an alkyl group, a para-substituted acetophenone corresponding to the target substance is reduced in ethanol using a reducing agent such as sodium borohydride,
When the substituent A is an alkoxy group, parahydroxyacetophenone is reacted with an alkyl halide corresponding to the substituent A of the target substance by the Williamson synthesis method to obtain a para-substituted acetophenone corresponding to the target substance. Examples of the reduction method include, but are not limited to.

In the present invention, as described above, the compound represented by the general formula (I) is reacted with trichloroethyl butyrate in an organic solvent using an enzyme having an esterase activity. Since the reaction is carried out using an enzyme having esterase activity, only the (+) form of the compound represented by the general formula (I) is selectively esterified to give the general formula (II): (In the formula, A is the same as above) and the compound represented by the general formula (I) is a general formula (III) which is a (-) form: A compound represented by the formula (A is the same as above) is obtained.

There are three possible isomers of trichloroethyl butyrate, all of which can be used effectively.
2,2-trichloroethyl butyrate is preferred because of its fast reaction rate.

Instead of the trichloroethyl butyrate, for example, 2-chloroethyl acetate, tributyrin, trichloroethyl acetate, ethyl acetate or the like may be used to esterify only the (+) form of the compound represented by the general formula (I). Although possible, it is not practical because the reaction rate is significantly slower than without trichloroethyl butyrate.

The enzyme having esterase activity may be an enzyme capable of asymmetrically esterifying only the (+) form of the compound represented by the general formula (I) in an organic solvent using trichloroethyl butyrate. It can be used without any restrictions, whether it is of microbial origin or animal origin,
Moreover, a commercially available product may be used. Specific examples of such an enzyme include, for example, Pseudomonas
Pseudomonas aeruginosa and other Pseudomonas species, Achromobacterium viscosum (Ac
Examples include, but are not limited to, enzymes obtained from microorganisms belonging to the genus Achromobacterium such as hromobacterium viscosm); enzymes produced from the pancreas of swine, which is an enzyme of animal origin.

Examples of commercially available products of these enzymes include lipase "Amano" P (manufactured by Amano Pharmaceutical Co., Ltd.), lipase Toyo (manufactured by Toyo Brewing Co., Ltd., trade name), pancreatin lipase (manufactured by Amano Pharmaceutical Co., Ltd.) , Trade name), pancreatin lipase (manufactured by Sigma Co., trade name) and the like.

In the present invention, the reaction is carried out in an organic solvent,
Since an organic solvent is used, when a conventional aqueous medium is used, the solubility of the compound represented by the general formula (I) is low, so that the productivity is low, and a compound which is substantially insoluble in the aqueous medium cannot be separated. The problems described above can be solved, the solubility of the compound represented by the general formula (I) can be increased to improve the productivity, and the compounds that cannot be resolved by the conventional method can be resolved.

The organic solvent dissolves the compound represented by the general formula (I), trichloroethyl butyrate, the compound represented by the general formula (II), and is not particularly limited as long as it does not inhibit the enzyme activity of the enzyme having esterase activity. It can be used without limitation.

Specific examples of such an organic solvent include ethyl ether, methyl ethyl ether, n-hexane, cyclohexane, n-heptane and the like.

The method of preparing the organic solvent containing the compound represented by the general formula (I), trichloroethyl butyrate and the enzyme having esterase activity in the present invention is not particularly limited, and for example, the compound represented by the general formula (I), trichloroethyl It may be prepared by adding an enzyme having butyrate and esterase activity to an organic solvent, or may be prepared by dissolving or dispersing them separately, or by mixing them by heating, but it is difficult to dissolve but can be dissolved by heating. It may be prepared by first dissolving only one and then adding another.

The use ratio of the compound represented by the general formula (I) and trichloroethyl butyrate is 2 when 1 mol of the compound represented by the general formula (I) is 1 mol ((+) form or 1 mol). It is preferable to use 0.5 to 2 mol of trichloroethyl butyrate relative to (calculated as mol) from the viewpoint of economically esterifying, and 1 to 1.5
More preferably, it is used in moles.

When the amount of trichloroethyl butyrate used is less than 0.5 mol, the amount of the trichloroethyl butyrate in the compound represented by the general formula (I) is less than that of the (+) form, so that all of the (+) form is esterified. On the other hand, when the amount exceeds 2 mol, the proportion of the used trichloroethyl butyrate that does not participate in the reaction increases, which is not economical.

The amount of the enzyme having esterase activity used is preferably 10 to 600 g, and more preferably 100 to 500 g, relative to 1 mol of the compound represented by the general formula (I). When the amount used is less than 10 g, the reaction rate is slow and economically disadvantageous, and when it exceeds 600 g, the enzyme is excessive compared to the reaction rate, which is economically disadvantageous.

Further, the ratio of the total amount of the compound represented by the general formula (I) and trichloroethyl butyrate used is 0.1 to 50% with respect to the weight of the solution obtained by dissolving these in an organic solvent.
(% By weight, the same applies hereinafter) is preferable, and more preferably 10
~ 30%. When the total amount of the compound represented by the general formula (I) and trichloroethyl butyrate to be used in the solution is less than 0.1%, the yield is low relative to the amount of the reaction solution and the cost is high. If it exceeds%, the concentration is too high, so that the reaction rate decreases and the yield decreases.

Since an enzyme having esterase activity is used in the present invention, a reaction temperature of usually 10 to 40 ° C, preferably 25 to 30 ° C is adopted.

The reaction time depends on the kind of the compound represented by the general formula (I) and the enzyme having the esterase activity, the use ratio of the compound represented by the general formula (I), trichloroethyl butyrate and the enzyme having the esterase activity, the stirring condition and the like. Differently, it cannot be specified in a general way, but it is usually 1 to 150
It is about 24 hours to 72 hours.

The completion of the reaction can be confirmed by the constant conversion rate of the compound represented by the general formula (I) into the ester as measured by gas chromatography.

The reaction mixture thus obtained is first filtered to remove the enzyme having esterase activity, such as by filtration. After that, if necessary, the organic solvent and the like are removed, and then the compound of the general formula (I
By separating the compound represented by I) from the compound represented by the general formula (III), the respective optically active substances are separated. Furthermore, when alcohol separated by transesterification or unreacted trichloroethyl butyrate is mixed in the thus separated product,
It may be purified by a method such as distillation. As a developing solvent for column chromatography, for example, a mixed solution of ethyl acetate / n-hexane (ethyl acetate / n-hexane having a volume ratio of 1/4 to 1/6), a mixed solution of chloroform / methanol (chloroform / Methanol is 1/10 to 1/20 by volume
It is better to use the above).

The separated enzyme having a used esterase activity can be reused.

Identification is carried out by measuring ¹ H-NMR spectrum, IR spectrum, specific optical rotation and the like.

In this way, (−) − represented by the general formula (III)
1-para-substituted phenyl ethanol with a yield of 80-98%,
Further, the (+)-1-para-substituted phenylethanolbutyric acid ester represented by the general formula (II) can be obtained in a yield of 80 to 98%.

The (-)-1-para-substituted phenylethanol represented by the general formula (III) usually has a property such as colorless oil or white crystals, although it depends on the number of carbon atoms of the substituted alkyl group or alkoxy group.

One method, the (+)-1-para-substituted phenylethanolbutyric acid ester represented by the general formula (II) has a property as a colorless oil and has an optical purity of about 100%. If necessary, the compound can be converted into (+)-1-para-substituted phenylethanol by hydrolysis, for example, by an enzymatic or chemical method.

The thus obtained (+)-1-para-substituted phenyl ethanol, (+)-1-para-substituted phenyl ethanol butyric acid ester and (-)-1-para-substituted phenyl ethanol are all medicines, agricultural chemicals, fragrances, It can be suitably used as a raw material for a ferroelectric liquid crystal or the like.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.

Example 1 (±) -1-paramethoxyphenylethanol 24.5 g (0.16 mol) and 2,2 in anhydrous diethyl ether 280 ml.
2,2-Trichloroethyl-n-butyrate 35.8 g (0.163
Then, 76.8 g of lipase "Amano" P (manufactured by Amano Pharmaceutical Co., Ltd., trade name) was added, and the mixture was reacted at 25 ° C. for 45 hours while stirring so as to disperse well. The reaction was carried out by tracing the conversion rate to the ester by gas chromatography every hour.

After confirming the completion of the reaction, lipase was removed by suction.

After concentrating the liquid, silica gel chromatography (n-
Hexane-ethyl acetate = 4/1) Fraction containing (-)-1-paramethoxyphenylethanol and 2,2,2-trichloroethanol and (+)-1-paramethoxyphenylethanol butyric acid ester and 2,2, Separated into two fractions containing 2-trichloroethyl-n-butyrate. After that, the two fractions were concentrated under reduced pressure and distilled under reduced pressure to obtain 11.6 g of (-)-1-paramethoxyphenylethanol.
(Yield 95%) and (+)-1-paramethoxyphenylethanol butyrate 17.8 g (Yield 94%) were obtained.

Of the obtained products, (+)-1-paramethoxyphenylethanol butyric acid ester was hydrolyzed with 200 ml of 1M ethanol solution of potassium hydroxide, concentrated, and extracted with ethyl ether to extract (+)-1-paramethoxyphenylethanol. 11.25 g (yield 90%) was obtained.

The obtained compound was analyzed by ¹ H-NMR spectrum analysis, I
It was analyzed by R spectrum analysis method and confirmed to be each compound. Further, the optical purity was determined by measuring the specific light rotation.

Specific optical rotation (-) - 1-p-methoxyphenyl ethanol [α] _D ²⁰ = -50.13 DEG _{(c = 1.12, CHCl 3)} (+) - 1- p-methoxyphenyl ethanol [α] _D ²⁰ = + 49.5 ° (C = 1.10, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ , δ value (ppm)) 1.46 (d, 3H), 2.07 (s, 1H), 3.79 (s, 3H), 4.
82 (q, 1H), 6.87 (d, 2H), 7.28 (d, 2H) IR (neat, cm ^-1 ) 3990, 2975, 2845, 1617, 1590, 1517, 1460, 1370, 1300, 1250, 1180, 1090, 1038, 1010, 900, 835, 810 Example 2 800 ml of anhydrous diethyl ether, 115 ± g of (±) -1-paraoctylphenylethanol in place of (±) -1-paramethoxyphenylethanol, 2,2,2- Trichloroethyl-n-butyrate (168 g) and lipase "Amano" P (manufactured by Amano Pharmaceutical Co., Ltd., trade name) 240 g were used in the same manner as in Example 1 except that (-)-1-paraoctylphenylethanol was used.
51.7 g (yield 90%) and (+)-1-paraoctylphenylethanol butyric acid ester 66.8 g (yield 89%) were obtained.

The (+)-1-paraoctylphenylethanol butyric acid ester was hydrolyzed in the same manner as in Example 1 to give (+)-1.
-Paraoctylphenyl ethanol 49.2g (yield 85%)
I got

Specific rotation (-)-1-paraoctylphenylethanol [α] _D ²⁰ = −30.02 ° (c = 1.07, CHCl ₃ ) (+)-1-paraoctylphenylethanol [α] _D ²⁰ = + 29.7 ° (C = 1.12, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ δ value (ppm) 0.89 (t, 3H), 1.30 (d, 1OH), 1.48 (d, 3H),
1.52 to 1.65 (m, 2H), 1.85 (s, 1H), 2.60 (t, 2
H), 4.86 (q, 1H), 7.17 (d, 2H), 7.28 (d ,, 2
H) IR (neat, cm ⁻¹ ) 3350, 2925, 2850, 1518, 1465, 1420, 1370, 1300, 1200, 1180, 1085, 1010, 900, 840, 820, 720 Example 3 Lipase “Amano” P ( Amano Pharmaceutical Co., Ltd., trade name)
(-)-1-Paramethoxyphenylethanol was used in the same manner as in Example 1 except that 76.8 g of pancreatin lipase (trade name, manufactured by Sigma) was used instead of 76.8 g.
11.0 g (yield 90%) and (+)-1-paramethoxyphenyl ethanol butyrate 16.1 g (yield 85%) were obtained.

The (+)-1-paramethoxyphenylethanol butyric acid ester was hydrolyzed in the same manner as in Example 1 to give (+)-1.
-9.8 g (yield 80%) of para-methoxyphenylethanol was obtained.

Specific optical rotation (-) - 1-p-methoxyphenyl ethanol [α] _D ²⁰ = -30.5 ° _{(c = 1.21, CHCl 3)} (+) - 1- p-methoxyphenyl ethanol [α] _D ²⁰ = + 45.3 ° (C = 1.30, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ , δ value (ppm)) 1.46 (d, 3H), 2.07 (s, 1H), 3.79 (s, 3H), 4.
82 (q, 1H), 6.87 (d, 2H), 7.28 (d, 2H) IR (neat, cm ^-1 ) 3390, 2875, 2845, 1617, 1590, 1517, 1460, 1370, 1300, 1250, 1180, 1090, 1038, 1010, 900, 835, 810 Example 4 Lipase "Amano" P (manufactured by Amano Pharmaceutical Co., Ltd., trade name)
(-)-1 in the same manner as in Example 1 except that 76.8 g of Lipase Toyo (trade name, manufactured by Toyo Shuzo Co., Ltd.) and 35.8 g of (±) -1-paramethoxyphenylethanol were used instead of 76.8 g. -Paramethoxyphenyl ethanol 16.5g
(Yield 92%) and (+)-1-paramethoxyphenylethanol butyrate 23.8 g (Yield 90%) were obtained.

The (+)-1-paramethoxyphenylethanol butyric acid ester was hydrolyzed in the same manner as in Example 1 to give (+)-1.
-Paramethoxyphenylethanol 15.4 g (86% yield)
I got

Specific optical rotation (-) - 1-p-methoxyphenyl ethanol [α] _D ²⁰ = -50.13 DEG _{(c = 1.12, CHCl 3)} , (+) - 1- p-methoxyphenyl ethanol [α] _D ²⁰ = + 49.5 (C = 1.10, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ , δ value (ppm)) 1.46 (d, 3H), 2.07 (s, 1H), 3.79 (s, 3H), 4.
82 (q, 1H), 6.87 (d, 2H), 7.28 (d, 2H) IR (neat, cm ^-1 ) 3390, 2975, 2845, 1617, 1590, 1517, 1460, 1370, 1300, 1250, 1180, 1090, 1038, 1010, 900, 835, 810 Example 5 (±) -1-paramethoxyphenylethanol 24.5 g
In the same manner as in Example 1 except that 26.0 g of (±) -1-parapentyloxyphenylethanol was used in place of (-)-1-parapentyloxyphenylethanol 1
2.7 g (yield 97%) and (+)-1-parapentyloxyphenyl ethanol butyrate 15.7 g (yield 90%)
I got

The (+)-1-parapentyloxyphenylethanol butyric acid ester was hydrolyzed in the same manner as in Example 1,
(+)-1-parapentyloxyphenylethanol 1
1.1 g (yield 86%) was obtained.

Specific optical rotation (-) - 1-parabens chill oxyphenyl ethanol [α] _D ²⁰ = -38.78 DEG _{(c = 1.07, CHCl 3)} , (+) - 1- parabens chill oxyphenyl ethanol [α] _D ²⁰ = + 37 .82 ° (c = 1.15, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ , δ value (ppm)) 0.93 (t, 3H), 1.30 to 1.47 (m, 4H), 1.49 (d, 3)
H), 1.72 to 1.82 (m, 2H), 1.83 (s, 1H), 3.94
(T, 2H), 4.84 (q, 1H), 6.87 (d, 2H), 7.28
(D, 2H) IR (neat, cm ^-1 ) 3360, 2960, 2930, 2875, 1618, 1587, 1518, 1477, 1395, 1370, 1300, 1243, 1179, 1090, 1078, 1010, 900 Example 6 ( ±) -1-paramethoxyphenylethanol 24.5g
In the same manner as in Example 1 except that 26.0 g of (±) -1-paraheptyloxyphenylethanol was used instead of (±) -1-paraheptyloxyphenylethanol 1.
2.7 g (yield 98%) and (+)-1-paraheptyloxyphenyl ethanol butyrate 15.6 g (yield 92%)
I got

The (+)-1-paraheptyloxyphenylethanol butyric acid ester was hydrolyzed in the same manner as in Example 1,
(+)-1-Paraheptyloxyphenylethanol 1
1.7 g (yield 90%) was obtained.

Specific rotation (-)-1-paraheptyloxyphenylethanol [α] _D ²⁰ = −33.78 ° (c = 1.12, CHCl ₃ ), (+)-1-paraheptyloxyphenylethanol [α] _D ²⁰ = + 34 .96 ° (c = 1.15, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ , δ value (ppm)) 0.89 (t, 3H), 1.20 to 1.40 (m, 10H), 1.48 (d, 3)
H), 1.70 ~ 1.82 (m, 2H), 1.98 (s, 1H), 3.92
(T, 2H), 4.81 (q, 1H), 6.86 (d, 2H), 7.26
(D, 2H) IR (neat, cm ^-1 ) 3350, 2960, 2930, 2875, 1618, 1585, 1520, 1470, 1400, 1360, 1300, 1258, 1176, 1090, 1080, 1065, 1040, 1020, 900 , 840, 820 Example 7 (±) -1-paramethoxyphenylethanol 24.5 g
(-)-In the same manner as in Example 1 except that 25.0 g of (±) -1-parapentylphenylethanol was used instead of (-)-
1-parapentylphenylethanol 12.0 g (yield 96
%) And (+)-1-parapentylphenylethanolbutyric acid ester (16.5 g, yield 92%).

The (+)-1-parapentylphenylethanol butyric acid ester was hydrolyzed in the same manner as in Example 1 to give (+)-1.
-Parapentylphenylethanol 11.1 g (yield 88.8
%).

Specific optical rotation (-) - 1-parabens chill phenylethanol [α] _D ²⁰ = -38.3 ° _{(c = 1.02, CHCl 3)} (+) - 1- parabens chill phenylethanol [α] _D ²⁰ = + 37.9 ° (C = 1.03, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ , δ value (ppm)) 0.91 (t, 3H), 1.25 to 1.38 (m, 4H), 1.48 (d, 3
H), 1.52 to 1.54 (m, 2H), 1.80 (s, 1H), 2.60
(T, 2H), 4.85 (q, 1H), 7.15 (d, 2H), 7.26
(D, 2H) IR (neat, cm ^-1 ) 3345, 2930, 2850, 1516, 1465, 1420, 1370, 1300, 1200, 1179, 1085, 1010, 900, 835, 720 Example 8 (±) -1 -Paramethoxyphenylethanol 24.5g
Instead of (±) -1-parabutylphenylethanol
(-)-1 in the same manner as in Example 1 except that 25.0 g was used.
12.2 g (yield 97%) of -parabutylphenylethanol and 17.2 g (93% yield) of (+)-1-parabutylphenylethanol butyric acid ester were obtained.

The (+)-1-parabutylphenylethanol butyric acid ester was hydrolyzed in the same manner as in Example 1 to give (+)-1-
Parabutyl phenyl ethanol 11.1 g (yield 88.8%) was obtained.

Specific optical rotation (-) - 1-p-butylphenyl ethanol [α] _D ²⁰ = -41.8 ° _{(c = 1.05, CHCl 3)} (+) - 1- p-butylphenyl ethanol [α] _D ²⁰ = + 40.8 ° (C = 1.21, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ , δ value (ppm)) 0.91 (t, 3H), 1.28 to 1.41 (m, 2H), 1.48 (d, 3)
H), 1.50 ~ 1.54 (m, 2H), 1.78 (s, 1H), 2.61
(T, 2H), 4.82 (q, 1H), 7.18 (d, 2H), 7.28
(D, 2H) IR (neat, cm ^-1 ) 3345, 2930, 2850, 1516, 1465, 1420, 1370, 1300, 1200, 1179, 1085, 1010, 900, 835, 720 Example 9 (±) -1 -Paramethoxyphenylethanol 24.5g
In the same manner as in Example 1 except that 25.0 g of (±) -1-paradecaneoxyphenylethanol was used instead of (±) -1-paradecaneoxyphenylethanol.
g (yield 97%) and (+)-1-paradecaneoxyphenylethanol butyrate 14.7 g (yield 96%) were obtained.

The (+)-1-paradecaneoxyphenylethanol butyric acid ester was hydrolyzed in the same manner as in Example 1 to obtain (+)-.
11.0 g of 1-paradecaneoxyphenylethanol (yield 9
0%).

Specific optical rotation (-) - 1-p-decane oxyphenyl ethanol [α] _D ²⁰ = -26.21 DEG _{(c = 1.25, CHCl 3)} (+) - 1- para decane oxyphenyl ethanol [α] _D ²⁰ = + 25. 41 ° (c = 1.15, CHCl ₃ ) ¹ H-NMR (300 MHz, in CDCl ₃ , δ value (ppm) 0.85 (t, 3H), 1.15 to 1.40 (m, 14H), 1.45 (d, 3)
H), 1.68 ~ 1.78 (m, 2H), 1.92 (s, 1H), 3.90
(T, 2H), 4.80 (q, 1H), 6.86 (d, 2H), 7.26
(D, 2H) IR (neat, cm ^-1 ) 3350, 2958, 2927, 2874, 1617, 1583, 1520, 1470, 1400, 1360, 1300, 1258, 1176, 1090, 1080, 1065, 1040, 1020, 900 , 840, 820 [Effects of the Invention] According to the method of the present invention, (±) -1-para-substituted phenylethanol can be easily and optically resolved into a range which cannot be optically resolved by the conventional method. .

Claims (2)

(57) [Claims] 1. A compound represented by the general formula (I): (Wherein A represents a linear alkyl group having 1 to 10 carbon atoms or a linear alkoxy group having 1 to 12 carbon atoms) represented by (±) -1-para-substituted phenylethanol and trichloroethylbutyrate as esterases. An enzyme having activity is allowed to act on the (+) form of the compound represented by the general formula (I) to give the general formula (II): (In the formula, A is the same as above), and then a (+)-1-para-substituted phenylethanolbutyric acid ester is formed, and then the compound represented by the general formula (II) and the general formula (III): (-)-1-para-substituted phenylethanol represented by the formula (wherein A is the same as above) is separated, and an optical resolution method of (±) -1-para-substituted phenylethanol is characterized. 2. The enzyme having esterase activity is an enzyme obtained from a microorganism belonging to the genus Pseudomonas or Achromobacterium or an enzyme obtained from the pancreas of an animal. Optical resolution method.