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Preparation method of 2-phenyl-1,3-propanediol

A technology of propylene glycol and phenyl, which is applied in the preparation of hydroxyl compounds, organic compounds, and carboxylate esters, can solve the problems of high cost of preparation methods and complicated post-treatment processes, and achieve remarkable technological progress, great application value, and The effect of high product purity and yield

Inactive Publication Date: 2015-12-16
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0007] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a method for preparing 2-phenyl-1,3-propanediol, which solves the problem of existing Technical problems such as high cost of preparation method and complicated post-treatment process

Method used

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  • Preparation method of 2-phenyl-1,3-propanediol
  • Preparation method of 2-phenyl-1,3-propanediol

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Embodiment 1

[0023] The synthesis of embodiment 1α-formylphenylacetic acid ethyl ester

[0024] a. Add 150mL anhydrous toluene, 16.4g (0.1mol) ethyl phenylacetate, 8.1g sodium methoxide solid into a 500mL four-neck flask, stir, heat, raise the temperature to 40-45°C, keep warm for 0.5h, add 8.9 g (0.15mol) of methyl formate in 50mL of toluene solution, after the dropwise addition, keep warm, and the plate reaction is completed, then cool down to -5 ~ 0°C, add 100mL of ice-water mixture dropwise to the flask under stirring, dropwise, Stand still, separate the water layer, adjust the pH to about 1-2 with 1mol / L sulfuric acid, extract with toluene (200mL×3), combine the toluene liquid, wash with saturated brine, dry with anhydrous sodium sulfate, and spin off the solvent 18g crude product , That is, ethyl α-formyl phenylacetate, the yield is 93.75%.

[0025] b. Add dried 150mL petroleum ether, 16.4g (0.1mol) ethyl phenylacetate, 8.1g sodium methoxide solid into a 500mL four-necked flask, sti...

Embodiment 22

[0026] The synthesis of embodiment 22-phenyl-1,3-propanediol

[0027] a. Add 2.3g of sodium borohydride and 100mL of absolute ethanol to a 250mL four-neck flask, stir, cool down below 0°C, add 4.8g of ethyl α-formylphenylacetate in 10mL of absolute ethanol solution dropwise, and add During the process, keep the temperature of the reaction solution below 0°C. After the dropwise addition is completed, keep warm for 0.5h and then raise the temperature to 50-55°C. React, spot the plate, and drop to room temperature after the reaction is completed. Add 1mol / L sulfuric acid dropwise to the flask to adjust the pH to about 3, raise the temperature to 50-55°C, keep warm for 2 hours, spin off the solvent, add water to dissolve, extract with ethyl acetate, spin dry, and use ethyl acetate:petroleum ether (1 : 3) dissolved, cooled and suction filtered, and washed with petroleum ether to obtain 2.3g. Yield 60.5%.

[0028] b. Add 3.8g of potassium borohydride, 100mL of absolute ethanol, an...

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Abstract

The invention provides a preparation method of 2-phenyl-1,3-propanediol. Ethyl phenylacetate and methyl formate have a condensation reaction in the presence of a specific solvent and a condensation agent, a mixture of ice and water is added to a reaction solution, a separated water layer is acidized and then extracted, organic layers are merged, the mixture is washed with a saturated saline solution, an organic solvent is recovered, alpha-formyl ethyl phenylacetate is obtained and is reduced through sodium borohydride in the specific solvent, acidification and extraction are performed, a mixed solvent of petroleum ether and ethyl acetate is heated, dissolved and cooled, solids are separated and washed with petroleum ether, and 2-phenyl-1,3-propanediol is obtained. The preparation method is simple and convenient to operate, the product purity and yield are high, and 2-phenyl-1,3-propanediol has very high application value.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to 2-phenyl-1,3-propanediol, specifically a preparation method of 2-phenyl-1,3-propanediol. Background technique [0002] 2-Phenyl-1,3-propanediol is an important pharmaceutical and fine chemical intermediate. 2-Phenyl-1,3-propanediol can be used in the synthesis of antiepileptic drug felbamate. (Li Chunyuan. Fecarbamate: A New Antiepileptic Drug[J]. Foreign Medicine-Synthetic Drugs, Biochemical Drugs, Preparations Volume, 1994,15(2):92-93.) [0003] There are three main synthetic routes for 2-phenyl-1,3-propanediol. [0004] 1) Using diethyl ether as a solvent, diethyl 2-phenyl-malonate was reduced with lithium aluminum hydride to obtain 2-phenyl-1,3-propanediol. Disadvantages: The cost of lithium aluminum hydride is high, while ether is volatile, flammable, and explosive. [0005] 2) Reduction of methyl 3-hydroxy-2-phenylpropionate with sodium borohydride using ethanol as a solve...

Claims

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Application Information

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IPC IPC(8): C07C29/147C07C29/14C07C33/26
CPCC07C29/147C07C29/14C07C67/343C07C33/26C07C69/738
Inventor 胡艳刘维俊林淑慧
Owner SHANGHAI INST OF TECH
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