Method for highly efficiently synthesizing 2-phenyl-1,3-propylene glycol

A high-efficiency, propylene glycol-based technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of hydroxyl compounds, etc., can solve the problems of low activity and long reaction time, so as to promote reduction reaction, increase yield and purity, shorten The effect of reaction time

Inactive Publication Date: 2018-04-10
SUZHOU GAIDE FINE MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when sodium borohydride is used for reduc...

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0022] A method for efficiently synthesizing 2-phenyl-1,3-propanediol, comprising the following steps:

[0023] (1) Add cetyltrimethylammonium bromide to the sodium hydroxide solution, stir and mix for 10 minutes, then add tetraethyl orthosilicate dropwise, stir at room temperature for 30 minutes after the dropwise addition, and ultrasonically treat in a water bath with a power of 500W 1h, a stable colloidal liquid was obtained; wherein, the mass ratio of cetyltrimethylammonium bromide, sodium hydroxide, and tetraethylorthosilicate was 0.3:1:0.01;

[0024] (2) Heat the above colloidal liquid at a heating rate of 5 °C / min to 120±5 °C, stir at constant temperature for 3 hours, then heat at a heating rate of 10 °C / min to 160-180 °C, stir and reflux for 6 hours, and the treatment ends After cooling to room temperature, the reaction product was distilled and concentrated under reduced pressure, and the obtained concentrate was vacuum-dried at 80°C, and the dried solid was calcined ...

Embodiment 2

[0028] A method for efficiently synthesizing 2-phenyl-1,3-propanediol, comprising the following steps:

[0029] (1) Add cetyltrimethylammonium bromide to the sodium hydroxide solution, stir and mix for 10 minutes, then add tetraethyl orthosilicate dropwise, stir at room temperature for 30 minutes after the dropwise addition, and ultrasonically treat in a water bath with a power of 500W 3h, a stable colloidal liquid was obtained; wherein, the mass ratio of cetyltrimethylammonium bromide, sodium hydroxide, and ethyl orthosilicate was 0.6:1:0.01;

[0030] (2) Heat the above colloidal liquid at a heating rate of 7 °C / min to 120±5 °C, stir at constant temperature for 5 hours, then heat at a heating rate of 15 °C / min to 180 °C, stir and reflux for 10 hours, and cool after the treatment To room temperature, the reaction product was concentrated by distillation under reduced pressure, and the obtained concentrate was vacuum-dried at 80°C, and the dried solid was calcined at 500°C for ...

Embodiment 3

[0034] A method for efficiently synthesizing 2-phenyl-1,3-propanediol, comprising the following steps:

[0035](1) Add cetyltrimethylammonium bromide to the sodium hydroxide solution, stir and mix for 10 minutes, then add tetraethyl orthosilicate dropwise, stir at room temperature for 30 minutes after the dropwise addition, and ultrasonically treat in a water bath with a power of 500W 1.5h, a stable colloidal liquid was obtained; wherein, the mass ratio of cetyltrimethylammonium bromide, sodium hydroxide, and tetraethylorthosilicate was 0.4:1:0.01;

[0036] (2) Heat the above colloidal liquid at a heating rate of 6 °C / min to 120±5 °C, stir at a constant temperature for 3.5 hours, then heat at a heating rate of 11 °C / min to 170 °C, stir and reflux for 7 hours, after the treatment After cooling to room temperature, the reaction product was concentrated by distillation under reduced pressure, and the obtained concentrate was vacuum-dried at 80°C, and the dried solid was calcined ...

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Abstract

The invention discloses a method for highly efficiently synthesizing 2-phenyl-1,3-propylene glycol. The method includes the following steps that firstly a silicate active agent is prepared; secondly,ethyl benzoacetate, methyl formate and diisopropyl carbodiimide are used as raw materials for condensation reaction; alpha-formyl ethyl phenylacetate is prepared; then sodium borohydride is used as ahydrogenation reductant, the prepared silicate active agent promotes a reduction reaction, and alpha-formyl ethyl phenylacetate is reduced to prepare 2-phenyl-1,3-propylene glycol. The 2-phenyl-1,3-propylene glycol prepared by the method is high in purity, high in yield, short in reaction time and low in cost.

Description

Technical field: [0001] The invention relates to the field of preparation of pharmaceutical intermediates, in particular to a method for synthesizing 2-phenyl-1,3-propanediol with high efficiency. Background technique: [0002] 2-Phenyl-1,3-propanediol is an important intermediate in the synthesis of a new antiepileptic drug felbamate (chemical name: 2-phenyl-1,3-propanediol dicarbamate). Therefore, the key to the synthesis of felbamate is the synthesis of 2-phenyl-1,3-propanediol. According to different raw materials, there are mainly three literature methods for preparing this compound so far. Method one: Bornemann etc. take diethyl ether as solvent, reduce 2-phenyl-diethyl malonate with lithium aluminum hydride; Method two: use ethanol as solvent, reduce 3-hydroxyl-2 phenylpropionate methyl with sodium borohydride Esters; Method Three: Using 2-nitro-2-phenyl-1,3-propanediol as raw material, hydrogenation reduction under Pd catalysis. Method 1 uses lithium aluminum hydr...

Claims

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Application Information

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IPC IPC(8): C07C33/26C07C29/159C07C67/313C07C69/738B01J21/16B01J37/03B01J37/08
CPCB01J21/16B01J37/038B01J37/082C07C29/159C07C67/313C07C69/738C07C33/26
Inventor 李晓明
Owner SUZHOU GAIDE FINE MATERIALS CO LTD
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