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Synthetic method for 1-phenyl-1,2-ethanediol

A technology of phenylethylene glycol and its synthesis method, which is applied in the fields of chemical instruments and methods, preparation of hydroxyl compounds, and preparation of organic compounds, etc., and can solve the problems of not meeting the requirements of green chemical development, low catalytic reaction efficiency, and difficulty in obtaining catalysts and other problems, to achieve the effect of easy to obtain catalyst, reduce industrial three wastes, and easy separation

Active Publication Date: 2018-06-08
CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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

Method used

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  • Synthetic method for 1-phenyl-1,2-ethanediol

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Example 1: Preparation of phenyl glycol

[0019] (1) Reaction: Add 5 g (41.67 mmol) of styrene oxide, 5 mg of tetrabutylammonium bromide, 0.48 g (4.17 mmol) of 2-chloroethylamine hydrochloride, and carbonic acid in a flask with a thermometer and reflux condenser. 0.34g (4.17mmol) of sodium hydride, 50mL of water, stirred, heated to reflux, and the reaction temperature was 40°C;

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

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

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

Embodiment 2

[0023] Example 2: Preparation of Phenyl Glycol

[0024] (1) Reaction: Add 10g (83.34mmol) of styrene oxide, 12mg of tetrabutylammonium bromide, 0.7g (6.03mmol) of 2-chloroethylamine hydrochloride, and carbonic acid in a flask with a thermometer and reflux condenser. 0.506g (6.03mmol) of sodium hydride, 120mL of water, stirred, heated to reflux, and the reaction temperature was 45°C;

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

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

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

Embodiment 3

[0028] Example 3: Preparation of Phenyl Glycol

[0029] (1) Reaction: Add 3g (25mmol) of styrene oxide, 24mg of tetrabutylammonium bromide, 0.29g (2.5mmol) of 2-chloroethylamine hydrochloride, and hydrogen carbonate in a flask with a thermometer and reflux condenser. 0.21g (2.5mmol) of sodium, 60mL of water, stirred, heated to reflux, and the reaction temperature was 37°C;

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

[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 desolvate under reduced pressure to obtain a white solid.

[0032] The yield of the prepared phenyl glycol is 96%, the purity is 98% (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 synthetic method for 1-phenyl-1,2-ethanediol. The synthetic method comprises the following steps: (1) performing a reaction: adding styrene oxide, a phase transfer catalyst, 2-chloroethylaminehydrochloride, an inorganic alkali and water into a flask with a thermometer and a reflux condenser pipe, performing stirring, and performing a heating reflux reaction; (2) performingend point monitoring: performing monitoring on the reaction of the step (1) by adopting an HPLC, and determining the reaction end point when the raw material styrene oxide disappears; and (3) performing extraction: when the reaction of the step (1) reaches the reaction end point, stopping heating, cooling the system to room temperature, performing extraction by using an organic solvent, separating and taking an organic layer, and performing decompression exsolution to obtain a white solid. The prepared product provided by the invention has high purity, a high yield and reduced three industrial waste (waste water, waste gas and solid waste), is friendly to the environment, and meets the requirements of the green chemistry process.

Description

Technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a method for synthesizing phenyl glycol. Background technique [0002] Phenyl glycol is an intermediate of organic synthesis. Because of its good light, heat, and chemical stability, it is widely used in the production of drugs, pesticides and food additives. The optically pure phenyl glycol obtained by chiral resolution is an important chiral alcohol module compound, an important material for materials science and drug development, and also an important material for preparing optically active pharmaceuticals, pesticides and functional materials. Intermediate. [0003] Defects and deficiencies of the prior art: At present, there are two main methods for preparing phenylethylene glycol in the world. One is to use styrene as the raw material. For example, in the literature (Carb on Tetmbromide: An Efficient Catalyst for Regioselective Ring Ope ning of Epoxides with Alcohols ...

Claims

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Application Information

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Patent Type & Authority Applications(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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