JPH01215298A - Method for optically resolving (+-)-1-para substituted phenylethanol - Google Patents

Abstract

PURPOSE:To industrially and advantageously subject the titled compound for medicine raw material, etc., to optical resolution, by reacting (+ or -)-1-para substituted phenylethanol and trichloroethylbutylate with an enzyme having esterase activity and then separating the resultant (+) product. CONSTITUTION:(+ or -)-1-para substituted phenylethanol expressed by formula I (A is 1-10C alkyl or 1-12C alkoxy) and trichloroethylbutylate are reacted with an enzyme having esterase activity in an organic solvent to convert (+)-1-para substituted phenylethanol compound among a compound expressed by formula I into (+)-1-para substituted phenylethanol lactic acid ester expressed by formula II and then the resultant compound expressed by formula II is separated from (-)-1-para substituted phenylethanol to optically resolve (+ or -)-1-para substituted phenylethanol.

Description

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

[Prior Art] Previously, there have been reports on the optical resolution method of -para-substituted phenylethanol. A method of asymmetrically hydrolyzing an ester in an aqueous solution (hereinafter referred to as asymmetric hydrolysis) (see JP-A-60-224494)
and ■ A method for asymmetric reduction of parahaloacetophenone by yeast (Tetrahedron Letters)
Dron 1etters), Volume 25, 3979-3
982 (1984)) is known.

However, in method (2), since the reaction is carried out in an aqueous system, the number of carbon atoms in the alkyl group, which is a substituent of the phenyl group of the l-substituted phenylethanol derivative used as the starting material, is 4.
Only the following branched-chain derivatives have been reported, and it is said that in the case of long-chain alkyl groups with 5 or more carbon atoms, the dispersibility in water decreases significantly and asymmetric hydrolysis becomes impossible. It has its drawbacks. In addition, since method (2) is an aqueous reaction similar to (2), it has the disadvantage that it is difficult to apply to derivatives in which the alkyl group, which is a substituent of the phenyl group, has 5 or more carbon atoms. This method has the disadvantage of being disadvantageous in terms of production equipment, production costs, etc.

[Problems to be Solved by the Invention] The present invention aims to solve the problems in the conventional method, such as not being able to be applied to substances with low solubility in water, and not being a simple and economical method. It has been done.

[Means to solve the problem].

The present invention is directed to the general formula (I): H (wherein A represents a linear alkyl group having 1 to 12 carbon atoms or a linear alkoxy group having 1 to 12 carbon atoms) in an organic solvent (± )-1-Para-substituted phenylethanol and trichloroethylbutyrate are treated with an enzyme having esterase activity to convert the compound represented by the general formula (■) into the (+) form of the compound represented by the general formula (■): 1st floor ( (wherein A is the same as above) is converted into (+)-1-substituted phenylethanolbutyric acid ester, and then a compound represented by general formula (1) and the general formula H (wherein A is as above) are prepared. The present invention relates to an optical resolution method for (±)-1-para-substituted phenylethanol, which is characterized in that it separates (-)-1-para-substituted phenylethanol represented by (the same).

[Example] In the present invention, a compound represented by the general formula (I): H (wherein A represents a straight-chain alkyl group having 1 to 10 carbon atoms or a straight-chain alkoxy group having 1 to 12 carbon atoms) ±>-1-para substituted phenylethanols are used.

As mentioned above, A in the general formula m is a straight chain alkyl group having 1 to 10 carbon atoms or a straight chain alkoxy group having 1 to 12 carbon atoms, and if the alkyl group or alkoxy group is not straight chain, Compounds derived from these as synthetic raw materials are pharmaceuticals,
If it is difficult to use in fields such as agricultural chemicals and liquid crystals, and if the alkyl group or alkoxy group has a carbon number outside the above range, the general formula (I
) is undesirable because the synthesis yield of the compound represented by the formula tends to be low.

Among the straight chain alkyl groups having 1 to 10 carbon atoms, those having 3 to 8 carbon atoms are used, and among the straight chain alkoxy groups having 1 to 12 carbon atoms, those having 3 to 10 carbon atoms are used for the pharmaceutical preparation. It is highly useful in fields such as , agricultural chemicals, and liquid crystals, especially in the field of liquid crystals, and furthermore, the synthesis yield of the compound represented by general formula (1) is good.

Specific examples of the compound represented by the general formula (1) having a linear alkyl group or a linear alkoxy group include (±)-1-paramethylphenylethanol, (±)-
1-parabutylphenylethanol, (±)-1-parapentylphenylethanol, (±)-1-paraoctylphenylethanol, (±)-1-paramethoxyphenylethanol, (±)-1-parapentyloxyphenyl Examples include ethanol, (±)-1-parabutyloxyphenylethanol, (±>-i-paradecaneoxyphenylethanol, (±)-1-paralauryloxyphenylethanol, etc.).

There are no particular limitations on the method for obtaining the compound represented by general formula (I), and any method may be used as long as the compound can be converted. For example, when substituent A in general formula (1) is an alkyl group, a method of reducing para-substituted acetophenone corresponding to the target substance in ethanol using a reducing agent such as sodium borohydride;
When substituent A is an alkoxy group, para-hydroxyacetophenone and a halogenated alkyl corresponding to substituent A of the target substance are reacted by the Williamson synthesis method to obtain a para-substituted acetophenone corresponding to the target substance, and then the above-mentioned Examples include, but are not limited to, methods such as a reduction method.

In the present invention, as described above, the compound represented by general formula (1) is reacted with trichloroethyl butyrate in an organic solvent using an enzyme having 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 (1) is selectively esterified, and the general formula (
If).

. (In the formula, A is the same as above) and the (-) form of the compound represented by the general formula m (I)
: The compound represented by H (wherein A is the same as above) can be used.

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

Instead of trichloroethyl butyrate, for example, 2-chloroethyl acetate, tributyrin, trichloroethyl acetate, ethyl acetate, etc. may be used to esterify only the (+) form of the compound represented by general formula (1). Although possible, it is not practical because the reaction rate is significantly slower than in the case of trichloroethyl butyrate.

The enzyme having esterase activity is any enzyme that can asymmetrically esterify only the (+) form of the compound represented by the general formula (1) in an organic solvent using trichloroethyl butyrate. It can be used without restriction and may be derived from microorganisms, animals, or commercially available products. Specific examples of such enzymes include Pseudomonas aeruginosa, which is an enzyme derived from microorganisms.
Pseudomonas spp., Achromobacterium viscosum, etc.
Examples include, but are not limited to, enzymes obtained from microorganisms belonging to the genus Achromobacterium such as Viscos Il; and animal-derived enzymes such as enzymes produced from pig pancreas.

Commercial products of these enzymes include, for example, lipase "Amano JP (manufactured by Ohno Seiyaku Aji, trade name), Lipase Toyo (manufactured by Toyo Jozo ■, trade name), pancreatin lipase (manufactured by Ohno Pharmaceutical ■, trade name), vancreatin Lipase (Sigma■
products, product names), etc.

In the present invention, the reaction is carried out in an organic solvent, but since an organic solvent is used, when a conventional aqueous medium is used, the solubility of the compound represented by general formula (I) is low, resulting in low productivity. It can solve the problem of not being able to split compounds that are not substantially soluble in the medium, and it can increase the productivity by increasing the solubility of the compound represented by the general formula (1), which could not be split by conventional methods. Effects can be changed, such as being able to divide things.

The organic solvent may be used in particular as long as it dissolves the compound represented by the general formula (1), trichloroethyl butyrate, and the compound represented by the general formula (summer) and does not inhibit the enzymatic activity of the enzyme having esterase activity. Can be used without restrictions.

Specific examples of such organic solvents include ethyl ether, methyl ethyl ether, n-hexane, cyclohexane, n-hebutane, and the like.

In the present invention, there are no particular limitations on the method for preparing the organic solvent containing the compound represented by general formula (I), trichloroethyl butyrate, and an enzyme having esterase activity.
For example, the compound represented by general formula (1), trichloroethyl butyrate, and an enzyme having esterase activity may be added to an organic solvent, or they may be dissolved or dispersed separately and mixed. Alternatively, it may be possible to prepare by first dissolving only those ingredients that are difficult to dissolve but can be heated and then adding other ingredients.

The usage ratio of the compound represented by the general formula (1) and trichloroethyl butyrate is 1 mole of the compound represented by the general formula (1) (if there are 1 mole each of the (+) and (-) forms, then 2 It is preferable to use 0.5 to 2 moles of trichloroethyl butyrate per mole (calculated as moles) from the viewpoint of economical esterification.
More preferably, 5 mol is used.

If the proportion of trichloroethyl butyrate used is less than 0.5 mol, the molar amount is smaller than the (+) form in the compound represented by general formula (1), so all of the (+) form is converted into ester. On the other hand, if the amount exceeds 2 moles, the proportion of trichloroethyl butyrate used that does not participate in the reaction increases, making it uneconomical.

Further, the amount of the enzyme having esterase activity used is 10 to 600 per mole of the compound represented by the general formula (1).
g is preferable, and 100 to 500 g is more preferable.

If the amount used is less than 10 8 , the reaction rate will be slow and it will be economically disadvantageous, and if it exceeds 600 g, the enzyme will be excessive compared to the reaction rate and will be economically disadvantageous.

Furthermore, the ratio of the total amount of the compound represented by the general formula (1) and trichloroethyl butyrate is 0.1 to 50% relative to the weight of the solution obtained by dissolving these in an organic solvent.
% (weight %, hereinafter the same) is preferable, and more preferably 10 to 30%.

The total usage ratio of the compound represented by general formula (1) and trichloroethyl butyrate to the solution is 0.
If the concentration is less than 1%, the yield will be low for the reaction branch point and the cost will be high; if it exceeds 50%, the concentration will be too high and the reaction rate will decrease, resulting in a low yield. .

In the present invention, since an enzyme having esterase activity is used, it is usually lO to 40°C, preferably 25 to 30°C.
A reaction temperature of is adopted.

The reaction time varies depending on the compound represented by general formula (I), the type of enzyme having esterase activity, the compound represented by general formula +1), the proportion of trichloroethyl butyrate and the enzyme having esterase activity used, stirring conditions, etc. , - cannot be generally specified, but usually 1 to 150
It is about an hour, and even about 24 to 72 hours.

Completion of the reaction is confirmed by the fact that the conversion rate of the compound represented by the general formula (I) into ester becomes constant, as measured by gas chromatography.

The reaction mixture thus obtained is first filtered to remove the enzyme having esterase activity. After that, if necessary, after removing the organic solvent etc., for example, by silica gel column chromatography, the general formula (I)
By separating the compound represented by formula (5) from the compound represented by general formula (5), each optically active substance is separated. Furthermore, if the thus separated product contains alcohol produced by the transesterification reaction or unreacted trichloroethyl butyrate, it may be purified by a method such as distillation. In addition, as a developing solvent for column chromatography, for example, ethyl acetate/
n-hexane mixture (ethyl acetate/n-hexane at a volume ratio of 174 to 1/6), chloroform/methanol mixture (chloroform/methanol at a volume ratio of 1/1)
0 to 1120) is preferably used.

The separated used enzyme having esterase activity can be reused.

Identification is performed by measuring I H-NMR spectrum, IR spectrum, specific optical intensity, and the like.

In this way, (-)-1- expressed by the general formula (5)
para-substituted phenylethanol with a yield of 80-98%,
Furthermore, (+)-1-para-substituted phenylethanolbutyric acid ester represented by general formula (I) can be obtained with a yield of 80 to 98%.

The (-)-1-para-substituted phenylethanol represented by the above general formula generally has a colorless oily state or a white crystalline state, although it varies depending on the number of carbon atoms in the substituted alkyl group or alkoxy group.

On the other hand, the (+)-1-para-substituted phenylethanolbutyric acid ester represented by the general formula (I) has a colorless oil-like property and an optical purity of approximately 100%. The compound can be converted into (+)-1-para-substituted phenylethanol by hydrolysis, for example, by enzymatic or chemical methods, if necessary.

The (+)-1-para-substituted phenylethanol, (+)-1-para-substituted phenylethanol butyric acid ester, and (-)-1-para-substituted phenylethanol obtained in this way can be used as pharmaceuticals, agricultural chemicals, fragrances, etc. It can be suitably used as a raw material for ferroelectric liquid crystals and the like.

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

Example 1 24.5 g (±)-1-paramethoxydiphenylethanol (0.18 mol) and 35.8 g (0.163 mol) 2.2.2-trichloroethyl-n-butyrate in 280 ml anhydrous diethyl ether. was dissolved, and then lipase ``Amano JP (manufactured by Ohno Pharmaceutical ■, trade name) 76
．． Add 8g and heat to 25°C while stirring to disperse well.
The reaction was carried out for 45 hours. The reaction was carried out by monitoring the conversion rate to ester by gas chromatography every hour.

After confirming that the reaction was completed, lipase was removed by suction filtration.

After concentrating the furnace solution, silica gel chromatography (n-
hexane/ethyl acetate-411) with a fraction containing (-)-1-paramethoxyphenylethanol and 2.2.2-trichloroethanol, and (+)-1-paramethoxyphenylethanolbutyric acid ester and 2.2. 2. −
It was separated into two fractions containing trichloroethyl-n-butyrate. Thereafter, each fraction of 27) was concentrated under reduced pressure and distilled under reduced pressure to obtain 11.6 g (yield 95%) of (-)-1-baramethoxyphenylethanol and (+)-
1-paramethoxyphenylethanol acetic acid ester 17
．． 8 g (yield 94%) was obtained.

Among the obtained products, (+)-1-paramethoxyphenylethanolbutyric acid ester was hydrolyzed with 200 ml of a 1M ethanol solution of potassium hydroxide, concentrated, and extracted with ethyl ether to obtain (+)-1-paramethoxyphenyl ethanolbutyrate. 11.25 g (yield 90%) of phenylethanol was obtained.

The obtained compounds were analyzed by II-NMR spectroscopy and IR spectroscopy, and confirmed to be each compound. Furthermore, the optical purity was determined by measuring the specific optical power.

Specific optical rotation (-)-1-paramethoxyphenylethanol (a)D
” --50,13” (c-1,12, CDCf3)
(+)-1-baramethoxyphenylethanol [a]
"-449,5@(cm1.lO, CDCf3)'
H-NMR (300 MHz, CDCf s, δ value (
pl) IB)) 1.46 (d, 3H) , 2.07 (
s, IH), 3.79 (s.

3B), 4.82 (Q, IH), 8.87 (d
, 2H), 7.28(d, 2H) IR (neatS es+-1) 339G, 2975.2845, 1617, 1590.
1517.1480, 1370, 1300, 1250,
1180, 1090.1038, 1010, 900
, 835, 81G Example 2 800 ml of anhydrous diethyl ether, 115 g of (±)-1-bara-octylphenylethanol instead of (±)-1-bara-methoxyphenylethanol, 2.2゜2-
The same procedure as in Example 1 was used except that 188 g of trichloroethyl-n-butyrate and 240 g of lipase Amano JP (manufactured by Ohno Pharmaceutical ■, trade name) were used. 90%) and (+)-1-baraoctyl phenylethanolbutyric acid ester (136.8 g (yield: 89%)).

The (+)-1-baraoctyl phenylethanolbutyric acid ester was hydrolyzed in the same manner as in Example 1 to form (+)-1-
Rose octylphenyl ethanol 49.2g (yield 85
%) was obtained.

Specific optical rotation (-) -1-baraoctylphenylethanol [α]
”--30,02° (c-1,07, CH(J s )
(+)-1-baraoctyl phenylethanol Cα)
”-429,7°(c-1,12,CHC#s)'
H-NMR (300 MHz, CDCf5, δ value (
pps) 0.89 (t, 3H), 1.10 (d,
10B), 1.48 (d.

8H), 1.52-1.85(i, 2H), 1.
85 (s, IH), 2.80 (t, 2H), 4.
88((1,LH), 7.17(d.

2H), 7.28(d, , 2H) IR(neat, am-”) 3350.2925.2850.1518.1485.
1420.1370.1300.1200.1180.
1085.101G, 900.84G, 820.72
0 Example 3 Lipase r Amano JP (manufactured by Ohno Pharmaceutical Flavor, trade name) 76
．． (-)-1-baramethoxyphenylethanol 1 was prepared in the same manner as in Example 1 except that 76.8 g of bankcreatine lipase (manufactured by Sigma, trade name) was used instead of 8 g.
1. Og (yield 90%) and 18.1 g (yield 85%) of (+)-1-paramethoxyphenylethanol acetic acid ester were obtained.

The (÷)-1-baramethoxyphenylethanolbutyric acid ester was hydrolyzed in the same manner as in Example 1 to form (+)-1-
Baramethoxyphenylethanol 9.8g (yield 80%
) was obtained.

Specific optical rotation (-)-1-paramethoxyphenylethanol [a) D
”--30,5° (c-1,21, CDCf3) (+
)-1-paramethoxyphenylethanol [α]D20
- +45.3° (c-1,30, CDCf3)'
H-NMR (300 MHz, CDCf s, δ value (ppm)) 1.48 (d, 3H), 2.07 (s
, LH), 3.79 (s.

3H), 4.82 (q, LH), 8.87 (d,
2H), 7.28(d, 2H) IR (neat s cm-') 3390.2975.2845.1617.1590.
1517, 1460, 1370, 1300, 1250,
1180, 1090.1038, 101G, 900
, 835, $10 Example 4 Lipase "Amano JP (manufactured by Ohno Pharmaceutical ■, trade name) 78
．． Instead of 8g, use 784g of Lipase Toyo (manufactured by Toyo Jozo ■, trade name) and 35.8g of (±)-1-paramethoxyphenylethanol. The procedure was the same as in Example 1 except that (
-)-1-paramethoxyphenylethanol 18.5g
(yield 92%) and (+)-1-paramethoxyphenylethanolbutyric acid ester 23.8g (yield 90%)
) was obtained.

The (+)-1-paramethoxyphenylethanolbutyric acid ester was hydrolyzed in the same manner as in Example 1 to form (+)-1-
Paramethoxyphenylethanol 15.4g (yield 8B
%) was obtained.

Specific optical rotation (-) -1-paramethoxyphenylethanol (a)
20--50.11° (c-1,12, CHC#s
), (+)-1-baramethoxyphenylethanol [α
] 20- +49.5°(c-1,10,C)ICl
3)'H-NMR (300MHz% in CDC#3,
δ value (ppm)) 1.48 (d, 3H), 2.07
(s, IH> , 3.79 (s138) , 4.8
2 (q% LH), 8.87 (d, 2H), 7
．． 28 (d, 2H) IR (neat scs-') 3390.29
75.2845, 1817, 1590, 1517.
1480, 1370, IHOl 1250, 1
180, 1090.1038, 1010.900. 8
35. 810 Example 5 (±) -1-paramethoxyphenylethanol 24
．． (±) -1-parabentyloxyphenylethanol instead of 5g28. Example 1 except that Of was used.
In the same manner as (-)-1-parapentyloxyphenylethanol 12.7sr (yield 97%) and (+)
15.7 g (yield: 90%) of -1-halapentyloxyphenylethanolbutyric acid ester was obtained.

The (+)-1-parapentyloxyphenylethanolbutyric acid ester was hydrolyzed in the same manner as in Example 1 to give (+)
-1-parapentyloxyphenylethanol 11.1
g (yield: 8B%).

Specific optical rotation (-)-1-parabentyloxyphenylethanol (CI) D20--88.78° (c-1,07,
CHCl5), (+)-1-parabentyloxyphenylethanol'H-NMR (300 MHz, in CDCl2, δ value (ppm)) 0.93 (t, 8H), 1.30-1
．． 47 (@, 48), 1.49 (d, 38)
, 1.72-1.82 (■, 2H) , 1.83
(s, LH), 3.94(t, 2H),
4.84 (q, IH), 6.87 (d, 2H)
, 7.28(d, 2H)IR(neat
%csa-')33BO12960,2930,
2875,181B, 1587.151B, 1477.
1395.1370.130G, 1243.1179.
1090.1078.101O1900 Example 6 (±)-1-paramethoxyphenylethanol 24.5
(-)-1-para-hebutyloxyphenylethanol 12.7 g (yield 98 %) and (+)-1-
Parahebutyloxyphenylethanolbutyrate 1
5.6 g (yield 92%) was obtained.

The (+)-1-parahebutyloxyphenylethanolbutyric acid ester was hydrolyzed in the same manner as in Example 1 to give (+)
-1-parahebutyloxyphenylethanol 11.7
+r (yield 90%) was obtained.

Specific optical rotation (-)-1-parahebutyloxyphenylethanol (a) D"--33,78° (c-1,12, CHC
l5), (+)-1-parahebutyloxyphenylethanol (a) n-14,98@(c-1,15, CHC#
s)' II-NMR (300MHz %CDCf
5, δ value (ppm)) 0.89 (t, 8H)
, 1.20-1.40 (■, l0H), 1.48 (d,
3J(), 1.70-1.82(layer, 21
(), 1.98 (8% IH), 3.92 (
t, 2H), 4.81(Q, IH),
6.86 (d, 28), 7.26 (d, 2H) IR
(neat S cm-”) 3350.29BO12930, 2875, 1618,
1585, 1520, 1470, 1400, 1360,
1300, 1258, 117B, 1090.1080.
1065.1040.1020.900. 84G
, 820 Example 7 (±)-1-paramethoxyphenylethanol 24.5
(−)-1-Parapentylphenylethanol 12.g was prepared in the same manner as in Example 1, except that 25.0 g of (±)-1-parapentylphenylethanol was used instead of (−)-1-parapentylphenylethanol.
osr (yield 9B%) and (+)-1-varapentylphenylethanol acetic acid ester 10.5g (yield 9B%)
2%).

The (10)-1-varapentylphenyl ethanolbutyric acid ester was hydrolyzed in the same manner as in Example 1 to form (+)-1-
Parapentylphenylethanol 11.1g (yield 88
．． 8%).

Specific optical rotation (-) -1-parapentylphenylethanol [α]
20--18.3° (c-1,02, CHCl5)
(+)-1-parapentylphenylethanol (α)D
"-437,9° (c-1,03, CDCf3)'
H-NMR (300 MHz, CDCf5, δ value (
ppm)) 0.91 (t, 8H), 1.25-1.
38 (m, 4H), 1.48 (d, 3H), 1
．． 52-1.54 (■, 2H), 1.80 (s.

1B), 2.60(t, 2H), 4.85(Q,
18), 7.15(d, 2H), 7.28(d,
2H) IR(neat scIl-') 3345.2930.2850.151B, 1485.
1420.1370.1300.1200.1179.
1085.1010.900.835.720 Example 8 (±> -t-paramethoxyphenylethanol 24
．． 12. (-)-1-Barabutylphenylethanol was prepared in the same manner as in Example 1, except that 25.0 g of (±)-1-barabutylphenylethanol was used instead of 5g.
i (yield 97%) and (+)-1-valabutylphenylethanolbutyric acid ester 17.2sr (yield 93%)
%) was obtained.

The (+)-1-valabutylphenylethanolbutyric acid ester was hydrolyzed in the same manner as in Example 1 to obtain 11.1 g of (+)-1-valabutylphenylethanol (yield 88.8
%) was obtained.

Specific optical rotation (-)-1-barabutylphenylethanol [α)D”
--41,8@(c-1,05,CHCl5)(+)
-1-Varabutylphenylethanol (rx)D"-
+40.8@(c-1,21', CHCl3)"
II-NMR (300MHz SCDCI s, δ value (ppm)) 0.91 (t, 3H), 1.28-1
．． 41 (s, 2H), 1.48 (d, 3H),
1.50-1.54 (m, 2H), 1.78 (s.

IH), 2.81(t, 2H), 4;82(q,
IH), 7.18(d, 2H), 7.28(d
12H) IR (neat s cm-') 3345.2930.2850.1511i, ■465
．． 1420.1370.1300.1200.1179
．． 1085.101O1900,1135,720 Example 9 (±)-1-paramethoxyphenylethanol 24.5
g instead of (±) -1-valadecaneoxyphenylethanol25. (-)-1-paradecaneoxyphenylethanol 11.9sr (yield 97%) and (+)-■-paradecaneoxyphenylethanolbutyric acid ester 14.
7g (yield 9B%) was obtained.

The (+)-1-valadecaneoxyphenylethanolbutyric acid ester was hydrolyzed in the same manner as in Example 1.+)-1
-paradecaneoxyphenylethanol 11, Osr
(yield 90%).

Specific optical rotation (=) -1-paradecaneoxyphenylethanol (a
) D”--28,21” (c-1,25, CHC
#s)(+)-1-paradecaneoxyphenylethanol [α) ”'+25.41” (c-1,15,
CHCl5)'H-NMR (300MHz, CD
In Cfs, δ value (ppm) 0.85 (t, 8H)
, 1.15-1.40 (s, 14H), 1.45 (d
, 88) , 1.88-1.78 (s, 2) 1) ,
1.92 (s, IH), 3.90 (t, 2H)
, 4.80 (q, IH), 11.86 (d, 2H)
, 7.26(d, 2H)IR(neat, an
-' ) 3350.2958.2927.2874.1617.
1583.1520.1470.1400.1380.
1300.1258.111B, 1090.1080.
1065.1040.1020.900, 840
, 82G [Effects of the Invention] According to the method of the present invention, it is possible to easily optically resolve (±>-1-para-substituted phenylethanol) to a range that could not be optically resolved by conventional methods.

Claims (1)

[Claims] 1 General formula (I) in an organic solvent: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A is a linear alkyl group having 1 to 10 carbon atoms or a straight chain alkyl group having 1 to 10 carbon atoms. -12 straight-chain alkoxy groups) represented by (±)-1-para-substituted phenylethanol and trichloroethyl butyrate are treated with an enzyme having esterase activity to form a compound of the general formula (I). The (+) body is represented by the general formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, A is the same as above) Then, the compound represented by the general formula (II) and the general formula (III): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (-)-1- represented by (in the formula, A is the same as above) A method for optical resolution of (±)-1-para-substituted phenylethanol, which comprises separating para-substituted phenylethanol. The enzyme having esterase activity is derived from the genus Pseudomonas or Achromobacterium.
The optical resolution method according to claim 1, wherein the enzyme is an enzyme obtained from a microorganism belonging to the genus or an enzyme obtained from an animal pancreas.