A kind of synthetic method of phenyl glycol

A technology of phenylethylene glycol and synthesis method, which is applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of organic compounds, etc., can solve the problems that do not meet the requirements of green chemistry development, the catalytic reaction efficiency is not high, and the catalyst is difficult to obtain and other problems, to achieve the effect of easy availability of catalyst, reduction of industrial three wastes, and easy separation

Active Publication Date: 2021-06-08
CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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  • Abstract
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Problems solved by technology

[0005] Afterwards, there have been reports in the literature that other catalysts were used to catalyze the synthesis of this substance. The reported catalysts are difficult to obtain, and the price is expensive, and the catalytic reaction efficiency is not high. Although the bromine addition reaction route has been applied in industrialization, it has relatively large pollution. , the defect of high environmental cost, does not meet the requirements of green chemical development

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  • A kind of synthetic method of phenyl glycol

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Experimental program
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Effect test

Embodiment 1

[0018] Embodiment 1: preparation of phenyl glycol

[0019] (1) Reaction: Add styrene oxide 5g (41.67mmol), tetrabutylammonium bromide 5mg, 2-chloroethylamine hydrochloride 0.48g (4.17mmol), carbonic acid Sodium hydrogen 0.34g (4.17mmol), water 50mL, stirring, heating to reflux, the reaction temperature is 40°C;

[0020] (2) End point monitoring: the reaction of step (1) is monitored by HPLC, and when the raw material styrene oxide disappears, it is the end point of the reaction;

[0021] (3) Extraction: When the reaction in step (1) reaches the end point, stop heating, cool the system to room temperature, extract with 80 mL of ethyl acetate, separate the ethyl acetate layer, and precipitate under reduced pressure to obtain a white solid.

[0022] The yield of phenylethylene glycol was 99%, the purity was 98.5% (as determined by HPLC), the melting point was 63-65° C., and the MS m / z was 161.05 (M+Na, 100).

Embodiment 2

[0023] Embodiment 2: preparation of phenyl glycol

[0024] (1) Reaction: Add styrene oxide 10g (83.34mmol), tetrabutylammonium bromide 12mg, 2-chloroethylamine hydrochloride 0.7g (6.03mmol), carbonic acid Sodium hydrogen 0.506g (6.03mmol), water 120mL, stirring, heating to reflux, the reaction temperature is 45°C;

[0025] (2) End point monitoring: the reaction of step (1) is monitored by HPLC, and when the raw material styrene oxide disappears, it is the end point of the reaction;

[0026] (3) Extraction: When the reaction in step (1) reaches the end point, stop heating, cool the system to room temperature, extract with 120 mL of ethyl acetate, separate the ethyl acetate layer, and precipitate under reduced pressure to obtain a white solid.

[0027] The yield of phenylethylene glycol was 97%, the purity was 96% (as determined by HPLC), the melting point was 63-65° C., and the MS m / z was 161.05 (M+Na, 100).

Embodiment 3

[0028] Embodiment 3: preparation of phenyl glycol

[0029] (1) Reaction: Add styrene oxide 3g (25mmol), tetrabutylammonium bromide 24mg, 2-chloroethylamine hydrochloride 0.29g (2.5mmol), bicarbonate Sodium 0.21g (2.5mmol), water 60mL, stirred, heated to reflux, the reaction temperature is 37°C;

[0030] (2) End point monitoring: the reaction of step (1) is monitored by HPLC, and when the raw material styrene oxide disappears, it is the end point of the reaction;

[0031] (3) Extraction: When the reaction in step (1) reaches the end of the reaction, stop heating, cool the system to room temperature, extract with 60 mL of ethyl acetate, separate the ethyl acetate layer, and precipitate under reduced pressure to obtain a white solid.

[0032] The yield of phenylethylene glycol was 96%, the purity was 98% (as determined by HPLC), the melting point: 63-65° C., MS m / z: 161.05 (M+Na, 100).

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Abstract

The invention provides a kind of synthetic method of phenylethylene glycol, and this synthetic method comprises the following steps: (1) reaction: add styrene oxide, phase transfer catalyst, 2-chloroethyl in the flask with thermometer, reflux condenser Amine hydrochloride, inorganic alkali, water, stirring, heating and reflux reaction; (2) End point monitoring: the reaction of step (1) is monitored by HPLC, when the raw material styrene oxide disappears, it is the end point of the reaction; (3) Extraction: When the reaction in step (1) reaches the end of the reaction, stop heating, cool the system to room temperature, extract with an organic solvent, separate the organic layer, and precipitate under reduced pressure to obtain a white solid. The prepared product has high purity and yield, reduces three industrial wastes, is environmentally friendly, and meets the requirements of green chemical technology.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of phenylethylene glycol. Background technique [0002] Phenylethylene glycol is an intermediate in organic synthesis, and is widely used in the production fields of drugs, pesticides and food additives due to its good light, heat and chemical stability. The optically pure phenylethylene glycol obtained by chiral resolution is an important chiral alcohol module compound, which is an important material for material science and drug development, and is also an important material for the preparation of optically active medicines, pesticides and functional materials. intermediate. [0003] Defects and deficiencies in the prior art: at present, there are mainly two methods for preparing phenylethylene glycol in the world, and one is by styrene as raw material, as Yadav J.S. et al. Ope ning of Epoxides with Alcohols and Water [J].Synthesis, 2005, 1 7:2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/10C07C33/26
CPCC07C29/106C07C33/26
Inventor 王凯陈强岳邦毅肖尖郝卫强陆国元张秀芹
Owner CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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