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Method for preparing p-hydroxy phenyl ethyl ketone compound through rearrangement reaction under catalysis of acidic ionic liquid

An acidic ionic liquid and a technology for p-hydroxyacetophenone, which is applied in the field of catalytic preparation of p-hydroxyacetophenone compounds, can solve the problems of serious environmental pollution, high corrosiveness, poor catalyst stability, etc., and achieves high reaction selectivity, selective The effect of specificity and high catalytic activity

Active Publication Date: 2013-10-23
DALIAN UNIV
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  • Application Information

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Problems solved by technology

[0009] The purpose of the present invention is to provide a kind of method for preparing p-hydroxyacetophenone compounds by Fries rearrangement aiming at the deficiencies such as high catalyst toxicity, high corrosiveness, serious environmental pollution, poor catalyst stability and difficulty in repeated use in the current technology. Acidic Ionic Liquid Catalyst

Method used

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  • Method for preparing p-hydroxy phenyl ethyl ketone compound through rearrangement reaction under catalysis of acidic ionic liquid
  • Method for preparing p-hydroxy phenyl ethyl ketone compound through rearrangement reaction under catalysis of acidic ionic liquid
  • Method for preparing p-hydroxy phenyl ethyl ketone compound through rearrangement reaction under catalysis of acidic ionic liquid

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Embodiment 1

[0025] Experimental method: Add 5mmol of phenyl acetate into a 25mL one-necked flask, add 5mmol of N - Ethylimidazole trifluoromethanesulfonate ionic liquid, the reaction was stopped after stirring at 60° C. for 12 hours. Add 2 mL of water to dilute, extract three times with 2 mL of ethyl acetate, and wash the ethyl acetate layer with anhydrous MgSO 4 Dry and distill under reduced pressure to obtain p-hydroxyacetophenone with a yield of 18%.

Embodiment 2

[0027] Experimental method: Add 5 mmol of phenyl acetate into a 25 mL one-necked flask, add 5 mmol of 2-picoline trifluoromethanesulfonate ionic liquid, stir and react at 60° C. for 12 h, then stop the reaction. Add 2 mL of water to dilute, extract three times with 2 mL of ethyl acetate, and wash the ethyl acetate layer with anhydrous MgSO 4 Dry and distill under reduced pressure to obtain p-hydroxyacetophenone with a yield of 16%.

Embodiment 3

[0029] Experimental method: Add 5 mmol of phenyl acetate into a 25 mL single-necked flask, add 5 mmol of tri-n-octylamine trifluoromethanesulfonate ionic liquid, stir and react at 60° C. for 12 h, then stop the reaction. Add 2 mL of water to dilute, extract three times with 2 mL of ethyl acetate, add 2 mL of water to dilute, extract three times with 2 mL of ethyl acetate, wash the ethyl acetate layer with anhydrous MgSO 4 Dry and distill under reduced pressure to obtain p-hydroxyacetophenone with a yield of 40%.

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Abstract

The invention provides a method for preparing a p-hydroxy phenyl ethyl ketone compound through Fries rearrangement reaction under catalysis of an acidic ionic liquid. The method comprises the following steps of: directly adding phenyl acetate to the ionic liquid, wherein the dosage of the ionic liquid is 10%-40% of the mole number of oligomers; next, reacting for 12-18 hours at a temperature ranging from 60 to 120 DEG C, thus obtaining p-hydroxy phenyl ethyl ketone without o-hydroxy phenyl ethyl ketone type product through extraction, drying and reduced pressure distillation. The ionic liquid applied to the method is used as a solvent and a catalyst, and is high in catalytic activity and selectivity; the dosage of the catalyst is low and the reaction yield is high; the use of other organic solvent and toxic catalyst is reduced, so that the corrosivity of the catalyst to equipment is reduced; the aftertreatment is simple and convenient.

Description

technical field [0001] The invention relates to a method for catalytically preparing p-hydroxyacetophenone compounds, more specifically, relates to a method for catalytically generating p-hydroxyacetophenone compounds by using an acidic ionic liquid through a Fries rearrangement reaction. Background technique [0002] The p-hydroxyacetophenone obtained by the method is an important synthon in organic synthesis, an important organic chemical raw material, an important intermediate in the pharmaceutical industry and perfume manufacturing industry. For example, p-hydroxyacetophenone can be used in the synthesis of pharmaceutical intermediates and feed additives, such as choleretic and asthma medicine Salbutamol, anti-inflammatory drug Bufexamac, etc. [0003] The Fries rearrangement method is the most commonly used route to prepare p-hydroxyaryl ketones. The catalyst used in the traditional Fries rearrangement method is AlCl 3 , Lewis acid such as trifluoromethanesulfonate or ...

Claims

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Application Information

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IPC IPC(8): C07C45/54C07C49/825
Inventor 王爱玲赵壮志李长平崔颖娜尹静梅郑学仿
Owner DALIAN UNIV
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