JPH0775594A - Production of optically active 1,2-diol - Google Patents

Abstract

PURPOSE:To obtain an optically active 1,2-diol useful as a synthetic raw material for medicines, agrochemicals, etc., having wide selectivity of the number of carbons and excellent optical purity efficiently in a high yield by reacting a specific enantiomer mixture of a specific carbonic acid ester under a specific condition. CONSTITUTION:An enantiomer mixture of a cyclic carbonic acid ester of formula I (R is alkyl) such as 4-methyl,-1,3-dioxolan-2-one is treated with a lipase of swine pancreas capable of selectively hydrolyzing the carbonic acid ester of one enantiomer of the mixture or a substance containing lipase of swine pancreas to form an optically active diol of formula II or formula III and an optically active carbonic acid ester of formula IV or formula V. The optically active 1,2-diol is separated from the optically active carbonic acid ester to collect the optically active 1,2-diol and the optically active carbonic acid ester is hydrolyzed in the presence of an alkali to provide the objective optically active 1,2-diol of formula II or formula III.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing optically active 1,2-diol, which is an important compound as a raw material for the synthesis of optically active drugs, agricultural chemicals, liquid crystals and the like.

[0002]

2. Description of the Related Art As a method for producing an optically active 1,2-diol, a method of optically resolving a racemic diol or a derivative thereof by an enzymatic reaction has been reported, but some problems remain. For example, the stereospecific butyrylation reaction of diols with lipase (J. Am. Chem. S.
oc.), 106 , 2687 (1984)) uses only 1,2-butanediol, and its applicability to 1,2-diol having a higher number of carbon atoms is unknown. The volume efficiency is low because it requires about 5 times as much esterifying agent. Further, stereospecific hydrolysis with a hydrolase epoxide (Journal of Organic Nick Chemistry (J.Org.Chem.), 54 .5978 ( 1989)) method using the linear 1, 2-diol can be obtained only with low optical purity, and its yield is low. Also, a stereospecific hydrolysis reaction of diacetate with lipase (J. Chem. Soc. Chem. Commu
n.), 49 (1991), Journal of Organics.
Chemistry (J. Org. Chem.), 54 , 2787 (1989))
Although a method utilizing is reported, these are optical resolution methods for cyclic 1,2-diols. Acyclic 1, which has high volumetric efficiency and high yield, and wide choice of carbon number of substrate 1,
The reality is that an effective optical resolution method for 2-diol has not been developed.

[0003]

Therefore, in the optical resolution of 1,2-diol by enzymatic reaction, the development of an effective optical resolution method of acyclic 1,2-diol, which has a wide range of choice of carbon number of the substrate, has been developed. Is desired. The present inventor, as a result of various studies, selected a carbon number by using a pig pancreatic lipase as a catalyst, selecting a cyclic carbonic acid ester as a new substrate for an enzymatic reaction, and performing a hydrolysis reaction. A method for producing two kinds of optically active acyclic 1,2-dioles having a wide range of the above was found, and the present invention was completed based on this finding. As is clear from the above description, the object of the present invention is to provide a stereospecific hydrolysis reaction of a cyclic carbonic acid ester using an enzyme, which has a high volume efficiency, a high yield, and a wide range of carbon number selection. A method of producing a cyclic 1,2-diol.

[0004]

The present invention has the following constitution. (1) A porcine pancreatic lipase or porcine pancreatic lipase capable of selectively hydrolyzing a carbonic acid ester bond of one enantiomer in the mixture to a mixture of enantiomers of a cyclic carbonic acid ester represented by the following chemical formula 6 By reacting a ze-containing substance, the optically active compound represented by the following chemical formula 7 or the following chemical formula 1,
2-diol and an optically active carbonic acid ester represented by the following Chemical formula 9 or Chemical formula 10 are produced to produce the optically active 1,2
-Diol and the optically active carbonic acid ester are separated to obtain the optically active 1,2-diol, and the optically active carbonic acid ester is hydrolyzed in the presence of an alkali to give the following compound 8 or A method for producing an optically active 1,2-diol, which comprises producing the optically active 1,2-diol represented by the following chemical formula 7.

[Chemical 6] (In the formula, R represents an alkyl group)

[Chemical 7] (In the formula, R represents an alkyl group)

[Chemical 8] (In the formula, R represents an alkyl group)

[Chemical 9] (In the formula, R represents an alkyl group)

[Chemical 10] (In the formula, R represents an alkyl group)

The enantiomeric mixture of cyclic carbonic acid esters used in the present invention is a mixture (racemic mixture) of two enantiomers of cyclic carbonic acid ester or a mixture containing them in unequal proportions. The cyclic carbonic acid ester mixture comprises 1,2-diol and methyl chloroformate, a chloroformic acid ester such as phenyl chloroformate or dimethyl carbonate, a carbonic acid diester such as diphenyl carbonate, pyridine, triethylamine, potassium carbonate, It can be synthesized by reacting in the presence of a base such as sodium methoxide or metallic sodium while being heated from room temperature to 120 ° C to 130 ° C in a solvent-free or organic solvent.

The porcine pancreatic lipase used in the present invention exerts a catalytic effect in the hydrolysis reaction, and may be a purified product or a crude product, for example, SIGMA CHEMICAL CO., Fluka Chemie AG (FLUKA). CH
EMIE AG), Katayama Chemical Co., Ltd., Tokyo Chemical Industry Co., Ltd.
Commercially available products can be used. Further, as the form thereof, either powder or granular form can be used.

Further, a carrier for immobilizing the above-mentioned porcine pancreatic lipase by a physical adsorption method, for example, a polymeric substance such as polystyrene, polypropylene, starch, gluten, activated carbon, porous glass, celite, zeolite, kaolinite, vent It is also possible to dry and use the immobilized lipase supported and immobilized on an immobilization carrier made of an inorganic material such as light, alumina, silica gel, hydroxyapatite, calcium phosphate, and metal oxide. Further, after the completion of the reaction, the immobilized lipase recovered from the reaction solution by filtration retains sufficient activity and stereoselectivity of the reaction, and thus can be repeatedly used.

The amount of porcine pancreatic lipase used is 0.1-5 times the weight (weight ratio) of the enantiomeric mixture of cyclic carbonates.
Is preferable, and 0.5-1 times amount (weight ratio) is more preferable. The type of water used in the hydrolysis reaction of the present invention is not limited, but from the viewpoint of stability, reaction rate and selectivity of porcine pancreatic lipase, a phosphate buffer solution having a pH of 6 to 8 or boric acid. A buffer solution such as a buffer solution is preferably used. The amount used varies depending on the cyclic carbonic acid ester used, but is 1-100 relative to the cyclic carbonic acid ester.
Double amount (weight ratio) is preferable.

The temperature of the hydrolysis reaction is appropriately in the range of 20 ° C to 60 ° C in view of the stability of porcine pancreatic lipase, but from the viewpoint of reaction rate, suppression of side reactions and selectivity, it is in the range of 20 ° C to 4 ° C.
It is more preferable to set it near 0 ° C. The reaction time varies depending on the type of cyclic carbonic acid ester used, and is usually 1-3 days when the reaction is stopped at a reaction rate of around 50%. The reaction rate can be examined by gas chromatography, liquid chromatography, NMR, etc., or by measuring the amount of carbon dioxide generated. Usually, the 1,2-diol represented by Chemical formula 7 is produced by the hydrolysis reaction with the lipase, but when the carbon number of the cyclic carbonic acid ester which is a mixture of enantiomers is long, the hydrolysis reaction with the lipase gives In some cases, the indicated 1,2-diol may be formed.

As a method for separating the optically active 1,2-diol and the optically active cyclic carbonic acid ester, for example, separation by column chromatography or distillation is adopted. Alkaline hydrolysis of an optically active cyclic carbonic acid ester is carried out in a mixed solvent of water with an organic solvent such as methanol, ethanol, dioxane, or tetrahydrofuran, lithium hydroxide, sodium hydroxide, potassium hydroxide or barium hydroxide. It is carried out by reacting the alkali metal hydroxide or the alkaline earth metal hydroxide.

The alkyl group of the cyclic carbonic acid ester which is a mixture of enantiomers usable in the present invention may be an unsubstituted alkyl group or a substituted alkyl group. Examples of the substituted alkyl group include, for example, a part of --CH ₂ --O-- there are over S-, over NH chromatography, chromatography N (CH ₃₎ over, Moshikuwa N (CH ₂ CH ₃₎ alkyl group which is substituted in the over or the like. The cyclic ester carbonate is exemplified below. 4-methyl-1,3-dioxolane-
2-one, 4-ethyl-1,3-dioxolan-2-one, 4-propyl-1,3-dioxolan-2-one,
4-Butyl-1,3-dioxolan-2-one, 4-pentyl-1,3-dioxolan-2-one, 4-hexyl-1,3-dioxolan-2-one, 4-heptyl-
1,3-dioxolan-2-one, 4-octyl-1,
3-dioxolan-2-one, 4-nonyl-1,3-dioxolan-2-one, 4-decyl-1,3-dioxolan-2-one, 4-undecyl-1,3-dioxolan-2-one, 4-dodecyl-1,3-dioxolane-
2-one, 4-tridecyl-1,3-dioxolane-2
-One, 4-tetradecyl-1,3-dioxolane-2
-One, 4-pentadecyl-1,3-dioxolane-2
-One, 4-hexadecyl-1,3-dioxolane-2
-One, 4-octadecyl-1,3-dioxolane-2
-One 4-decyloxymethyl-1,3-dioxolan-2-one, 4-decylthiomethyl-1,3-dioxolan-2-one, 4-decylaminomethyl-1,3-dioxolan-2-one, 4- (4-decylphenyloxymethyl ) -1,3-Dioxolan-2-one, 4-diethylaminomethyl-1,3-dioxolan-2-one.

The optically active 1,2-diol represented by Chemical formula 7 and the optically active 1, represented by Chemical formula 1, which can be produced by the present invention.
The following can be illustrated as 2-diol. (S) -1,2-propanediol, (R) -1,
2-propanediol, (S) -1,2-butanedio-
(R) -1,2-butanediol, (S) -1,2
-Pentandiole, (R) -1,2-pentanedio-
, (S) -1,2-hexanediol, (R) -1,
2-hexanediol, (S) -1,2-heptanediol, (R) -1,2-heptanediol, (S) -1,2-octanediol, (R) -1,2- Octanediol, (S) -1,2-nonanediol, (R) -1,2-nonanediol, (S) -1,2-decandiole, (R) -1,2-decandiole -R, (S) -1,2-undecanediol, (R) -1,2-undecanediol, (S) -1,2-dodecanediol,
(R) -1,2-dodecandiol, (S) -1,2-
Tridecandiole, (R) -1,2-tridecandiole, (S) -1,2-tetradecandiole,
(R) -1,2-tetradecandioyl, (S) -1,
2-Pentadecandiole, (R) -1,2-Pentadecandiole, (S) -1,2-Hexadecandiole
, (R) -1,2-hexadecandioyl, (S) -1,2-heptadecandioyl, (R) -1,2-heptadecandiole, (S) -1,2-octadecandio- (R) -1,2-octadecanediol, (S)
-1,2-Nonadecandiole, (R) -1,2-Nonadecandiole, (S) -1,2-icosanediol,
(R) -1,2-icosanediol, (S) -3-decyloxy-1,2-propanediol, (R) -3-decyloxy-1,2-propanediol, (S) -3-decylthio-1,2-propanediol ,, (R) -3
-Decylthio-1,2-propanediol, (S) -3
-Decylamino-1,2-propanediol, (R)-
3-decylamino-1,2-propanediol, (S)
-3- (4-decylphenyloxy) -1,2-propanediol, (R) -3- (4-decylphenyloxy) -1,2-propanediol, (S) -3-diethylamino-1,2 -Propanediol and (R) -3-diethylamino-1,2-propanediol.

More specifically, the production method of the present invention will be described. First, a cyclic carbonic acid ester which is a mixture of enantiomers is suspended in a phosphate buffer solution having a pH of 7, for example, and a predetermined amount of porcine pancreatic lipase is added and stirred. And carry out the reaction. The reaction is stopped at a reaction rate suitable for the substrate, for example, a reaction rate of 30 to 50%, the reaction mixture is filtered, and the reaction product is extracted with an organic solvent.
In particular, when the produced optically active 1,2-diol has high water solubility, the reaction mixture is filtered and concentrated, and then the reaction product is extracted with an organic solvent. Then, from the reaction product, an optically active substance, that is, (S) -1,2-diol or (R) -1,2-diol and an R-form cyclic carbonic acid ester or an S-form cyclic carbonic acid ester is added. To separate. In this case, as a specific separation method, separation by column chromatography, distillation or the like is adopted. The separated R-form or S-form cyclic carbonic acid ester is alkali-hydrolyzed with potassium hydroxide or the like in a water-methanol mixed solvent, and the product is extracted with an organic solvent to obtain an optically active (R)-
Isolate 1,2-diol or (S) -1,2-diol.

[0014]

EXAMPLES The present invention will be described in more detail with reference to Production Examples and Examples of a mixture of enantiomers of cyclic carbonic acid ester used in the present invention, but the present invention is not limited thereto.

(Production Example 1) 1,2-butanediol 2
0.0 g (222 mmol), diethyl carbonate 29.0 g
(245 mmol), and 0.90 g of potassium carbonate
The mixture of (6.5 mmol) was heated and stirred, and the produced ethanol was distilled off. The residue was distilled under reduced pressure, 4-ethyl-
1,3-Dioxolan-2-one 14.8 g (127 m
mol) was obtained with a yield of 57%. Physical properties of 4-ethyl-1,3-dioxolan-2-one bp. ^{99-103 ℃ / 8x10 2 Pa 1 H} -NMR (CCl 4) δ 1.00 (t, J = 7H
z, 3H), 1.5-2.1 (m, 2H), 3.8-
5.0 (m, 3H); IR (KBr plate)
1800 (C = O) cm ^-1

(Production Example 2) 1,2-Pentanediol 2
0.0 g (192 mmol), dimethyl carbonate 19.0 g
(211 mmol), and 0.77 g of potassium carbonate
The mixture of (5.6 mmol) was heated and stirred, and the produced methanol was distilled off. The residue was distilled under reduced pressure, and 4-propyl-1,3-dioxolan-2-one 15.1 g (116
mmol) was obtained with a yield of 60%. Physical properties of 4-propyl-1,3-dioxolan-2-one bp. 103-107 ° C./8×10 ² Pa ¹ H-NMR (CCl ₄ ) δ 1.00 (t, J = 6H
z, 3H), 1.6-2.1 (m, 4H), 3.9-
5.0 (m, 3H); IR (KBr plate)
1800 (C = O) cm ^-1

(Production Example 3) In accordance with Production Example 1, 1, 2
4-Butyl-1,3-dioxolan-2-one was obtained from -hexanediol in a yield of 67%. Physical property values of 4-butyl-1,3-dioxolan-2-one bp. 108-110 ° C./7×10 ² Pa ¹ H-NMR (CCl ₄ ) δ 0.93 (t, J = 6H
z, 3H), 1.1-2.1 (m, 6H), 3.9-
5.0 (m, 3H); IR (KBr plate)
1800 (C = O) cm ^-1

(Production Example 4) 1,2-octanediol 2
0.0 g (137 mmol), diethyl carbonate 17.9 g
(152 mmol), and potassium carbonate 0.55 g
The mixture of (4.0 mmol) was heated and stirred, and the produced ethanol was distilled off. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 1: 1) to give 4-hexyl-1,3-dioxolan-2-one 2
0.3 g (118 mmol) was obtained with a yield of 86%. Physical property value of 4-hexyl-1,3-dioxolan-2- ^{one 1} H-NMR (CCl ₄ ) δ 0.9 (t, J = 5H
z, 3H), 1.1-2.1 (m, 10H), 3.8-
5.0 (m, 3H); IR (KBr plate)
1800 (C = O) cm ^-1

(Production Example 5) In accordance with Production Example 4, 1, 2
4-Octyl-1,3-dioxolan-2-one was obtained from decandiol in a yield of 55%. Physical property value of 4-octyl-1,3-dioxolan-2- ^{one 1} H-NMR (CCl ₄ ) δ 0.90 (t, J = 5H
z, 3H), 1.1-2.1 (m, 14H), 3.8-
4.9 (m, 3H); IR (KBr plate)
1800 (C = O) cm ^-1

(Production Example 6) In accordance with Production Example 4, 1, 2
4-decyl-1,3-dioxolan-2-one was obtained from -dodecanediol in a yield of 82%. Physical property value of 4-decyl-1,3-dioxolan-2- ^{one 1} H-NMR (CCl ₄ ) δ 0.90 (t, J = 5H
z, 3H), 1.1-2.1 (m, 18H), 3.8-
4.9 (m, 3H); IR (KBr plate)
1800 (C = O) cm ^-1

(Production Example 7) In accordance with Production Example 4, 1, 2
4-dodecyl-1,3-dioxolan-2-one was obtained from tetradecandioyl in a yield of 79%. Physical property value of 4-dodecyl-1,3-dioxolan-2- ^{one 1} H-NMR (CCl ₄ ) δ 0.90 (t, J = 5H
z, 3H), 1.1-2.1 (m, 22H), 3.8-
4.9 (m, 3H); IR (KBr plate)
1800 (C = O) cm ^-1

(Example 1) 2.00 g of 4-octyl-1,3-dioxolan-2-one obtained in Preparation Example 5
(9.99 mmol), porcine pancreatic lipase (Lipase)
1.0 g of Sigma type II) and 0.7 mol · dm ⁻³ of phosphate buffer (pH = 7.0)
40 cm ³ of the mixture was stirred at room temperature for 22 hours. Ethanol (20 cm ³⁾ and Celite (5 g) were added to the reaction mixture, the mixture was stirred, and the reaction mixture was filtered using Celite. The celite added to the reaction solution and the celite used for filtration were treated with ethanol.
It was washed with 20 cm ³ of ethanol, the ethanol used for washing and the filtrate were combined, and concentrated under reduced pressure. Ethanol was added to the concentrated residue, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (hexane / ethyl acetate = 2: 1 to 1: 2),
0.523 g of (S) -1,2-decandiole (3.0
0 mmol) and (R) -4-octyl-1,3-dioxolan-2-one 1.17 g (5.86 mmol)
Were obtained in yields of 30% and 59%, respectively. Separated (R)
-4-octyl-1,3-dioxolan-2-one with 8.2 cm ³ of methanol and 10 wt% potassium hydroxide 8.
After adding 2 cm ³ and stirring at room temperature for 3 hours, 1 mol · dm
^-3 Neutralize the reaction solution with hydrochloric acid 15cm ³ and add ethyl acetate 20c.
Extracted 3 times with m ³ . The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give (R) -1,
1.01 g (5.81 mmol) of 2-decanediol was obtained with a yield of 58%. Physical properties (S)-1,2-Dekanjio - le: [α] _D ²⁵ -11.
6 ° (c 0.555, MeOH), optical purity 89% (R) -1,2-decandioyl: [α] _D ²⁵ +6.1
3 ° (c 0.555, MeOH), optical purity 47%
(Literature (Agric. Biol. Chem.), 55 , 1877 (199
1)): [α] _D ²⁹ + 13.0 ° (c 0.55, MeO
H), 100% ee)

(Example 2) (S) and (R) -1,2 in the same manner as in Example 1 except that 4-ethyl-1,3-dioxolan-2-one obtained in Production Example 1 was used. -Butanediol was obtained in yields of 24% and 46%, respectively. Physical property value (S) -1,2-butanediol: [α] _D ²⁵ -4.7
7 ° (c 2.64, EtOH), optical purity 30% (reference value (Journal of Organic Chemistry
(J. Org. Chem.), 52 , 2608 (1987)): [α] _D ²² -1.
5.35 ° (c2.60, EtOH), 98% ee) (R) -1,2-butanediol: [α] _D ²⁵ +2.1
4 ° (c 2.64, EtOH), optical purity 14%

Example 3 (S) and (R) -1, in accordance with Example 1 except that 4-propyl-1,3-dioxolan-2-one obtained in Preparation Example 2 was used. 2-Pentanediol was obtained in yields of 14% and 40%, respectively. Physical property value (S) -1,2-pentandiol: [α] _D ²⁵ -1
3.5 ° (c 1.16, EtOH), optical purity 58%
(Literature (Agric. Biol. Chem.), 54 , 1819 (199
0)): [α] _D ²⁰ −23.2 ° (c 1, EtOH),
100% ee) (R) -1,2-pentandiol: [α] _D ²⁵ +7.
63 ° (c 0.996, EtOH), optical purity 33%

Example 4 (S) and (R) -1, in accordance with Example 1 except that 4-butyl-1,3-dioxolan-2-one obtained in Production Example 3 was used. 2-Hexanediol was obtained in yields of 45% and 51%, respectively. Physical property value (S) -1,2-hexanediol: [α] _D ²⁴ -1
5.6 ° (c 1.01, EtOH), optical purity 71%
(Literature (Agric. Biol. Chem.), 54 , 1819 (199
0)): [α] _D ²⁰ −22.1 ° (c 1, EtOH),
100% ee) (R) -1,2-hexanediol: [α] _D ²⁴ +1
5.1 ° (c 1.02, EtOH), optical purity 68%

Example 5 (S) and (R) -1, in accordance with Example 1 except that 4-hexyl-1,3-dioxolan-2-one obtained in Production Example 4 was used. 2-Octanediol was obtained in yields of 24% and 56%, respectively. Physical property value (S) -1,2-octanediol: [α] _D ²⁵ -1
6.2 ° (c 1.00, EtOH), optical purity 83%
(Literature (Agric. Biol. Chem.), 54 , 1819 (199
0)): [α] _D ²⁰ -19.0 ° (c 1, EtOH),
97% ee) (R) -1,2-octanediol: [α] _D ²² +6.
77 ° (c 1.00, EtOH), optical purity 35%

Example 6 (S) and (R) -1, in accordance with Example 1 except that 4-decyl-1,3-dioxolan-2-one obtained in Production Example 6 was used. 2-Dodecandiol was obtained in yields of 38% and 50%, respectively. Physical property value (S) -1,2-dodecandiol: [α] _D ²⁵ -9.
90 ° (c 2.50, EtOH), optical purity 87%
(Journal of Organic Chemistry (J. Org. Chem.), 51 , 5353 (1986)): [α] _D ²⁰ −
10.1 ° (c2.55, EtOH), 89% ee) (R) -1,2-dodecanediol: [α] _D ²⁵ +7.
51 ° (c 2.53, EtOH), optical purity 66%

(Example 7) In accordance with Example 1 except that 4-dodecyl-1,3-dioxolan-2-one obtained in Production Example 7 was used, (S) and (R) -1, 2-Tetradecanediole was obtained in yields of 37% and 50%, respectively. The optical purity was determined by reacting with 4-methylphenylsulfonyl chloride in pyridine to induce 2-hydroxy-1- (4-methylphenylsulfonyloxy) tetradecane, and then performing high-performance liquid chromatography (HPL).
C) (CHIRALCEL OD, hexane / 2-propanol = 97: ³ , 0.7 cm ³ · min ⁻¹ ) The absolute configuration of each was estimated by comparing the sign of its optical rotation and the order of the two peaks in the above HPLC with those of the other 1,2-alkanediols. Physical properties (S)-1,2-tetradecane Geo - le: [α] _D ²⁵ -
6.50 ° (c 2.0, EtOH), optical purity 55%
ee (R) -1,2-tetradecandiole: [α] _D ²⁴ +
4.70 ° (c 2.0, EtOH), optical purity 41%
ee

[0029]

INDUSTRIAL APPLICABILITY According to the present invention, 1,2-porcine lipase, which is an enzyme preparation which is inexpensive and can be stably obtained, is used.
By stereoselectively hydrolyzing a cyclic carbonic acid ester of diol, an acyclic optically active (S) -1,2-diol and (R) -1 having a wide range of carbon numbers can be easily prepared. ，
2-diol can be obtained.

Claims (1)

[Claims] 1. A porcine pancreatic lipase or porcine pancreas capable of selectively hydrolyzing a carbonic acid ester bond of one enantiomer in the mixture to a mixture of cyclic carbonic acid ester enantiomers represented by the following chemical formula 1. By causing a lipase-containing substance to act, an optically active 1,2-diol represented by the following chemical formula 2 or the following chemical formula 3 and an optically active carbonic acid ester represented by the following chemical formula 4 or the following chemical formula 5 are produced. While separating the optically active 1,2-diol and the optically active carbonate to obtain the optically active 1,2-diol,
The optically active carbonic acid ester is hydrolyzed in the presence of an alkali to give an optically active compound represented by the following chemical formula 3 or chemical formula 1,
Optical activity 1, characterized by producing 2-diol
A method for producing 2-diol. [Chemical 1] (In the formula, R represents an alkyl group) (In the formula, R represents an alkyl group) (In the formula, R represents an alkyl group) (In the formula, R represents an alkyl group) (In the formula, R represents an alkyl group)