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Method for synthesizing p-hydroxyacetophenone compounds

A technology of p-hydroxyacetophenone and synthetic method, which is applied in the field of catalytic preparation of p-hydroxyacetophenone compounds, can solve the problems of high toxicity and volatility of catalysts, excessive catalyst dosage, and unsuitability for industrial production, etc., and achieve high yield , friendly to the environment and wide application range

Inactive Publication Date: 2019-01-11
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these catalysts themselves have high toxicity and volatility, and are highly corrosive to instruments and equipment; the catalyst is used in excessive amounts, and the price is expensive, so it is not suitable for industrial production; therefore, a class of mild, green, and environmentally friendly catalysts are designed for Fries rearrangement reaction, the research on the synthesis of p-hydroxyphenyl ketones is of great significance

Method used

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  • Method for synthesizing p-hydroxyacetophenone compounds
  • Method for synthesizing p-hydroxyacetophenone compounds
  • Method for synthesizing p-hydroxyacetophenone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Experimental method: 10mmol of DES catalyst [ChCl][ZnCl 2 ] 2 , 10mmol of phenyl acetate was added into a 50mL three-neck flask, stirred and reacted at 40°C for 30min, and detected by TLC, phenol was generated. After stirring for 3 h, no product was detected by TLC. After stirring and reacting for 12 hours, there was no change, so the reaction was stopped. Therefore [ChCl][ZnCl 2 ] 2 When the ratio of material to raw material is 1:1, only phenol is produced at 40°C.

[0023] Reaction equation:

[0024]

Embodiment 2

[0026] Experimental method: 20mmol of DES catalyst [ChCl][ZnCl 2 ] 2 , 10mmol of phenyl acetate was added into a 50mL three-neck flask, stirred and reacted at 40°C for 30min, and detected by TLC, phenol was generated. After stirring for 3 h, no product was detected by TLC. After stirring and reacting for 12 hours, there was no change, so the reaction was stopped. Therefore [ChCl][ZnCl 2 ] 2 When the ratio of material to raw material is 2:1, only phenol is produced at 40°C.

[0027] Reaction equation:

[0028]

Embodiment 3

[0030] Experimental method: 30mmol of DES catalyst [ChCl][ZnCl 2 ] 2 , 10mmol of phenyl acetate was added into a 50mL three-neck flask, stirred and reacted at 40°C for 30min, and detected by TLC, phenol was generated. After stirring for 3 h, no product was detected by TLC. After stirring and reacting for 12 hours, there was no change, so the reaction was stopped. Therefore [ChCl][ZnCl 2 ] 2 When the ratio of material to raw material is 3:1, only phenol is produced at 40°C.

[0031] Reaction equation:

[0032]

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Abstract

The invention relates to a method for synthesizing p-hydroxyacetophenone compounds. The method concretely comprises the following steps: synthesizing a DES catalyst from choline chloride and zinc chloride according to a molar ratio of 1:2, and reacting phenyl acetate compounds used as a substrate at 40-90 DEG C under a solvent-free condition for 0.5-3 h with the DES as the catalyst to prepare thep-hydroxyacetophenone compounds. No other solvents are added to the reaction system in the preparation process of the p-hydroxyacetophenone compounds, and the DES is used as the reaction catalyst anda solvent. The DES can be repeatedly used, and is green and environmentally friendly. The preparation method has the advantages of simple process, simplicity and convenience in reaction post-treatment, greenness and environmental protection.

Description

technical field [0001] The invention relates to a method for catalyzing the preparation of p-hydroxyacetophenone compounds, more specifically, to a method for preparing p-hydroxyacetophenone compounds by catalyzing a Fries rearrangement reaction with a deep eutectic solvent. Background technique [0002] Hydroxyaryl ketones are important synthons in organic synthesis, important organic chemical raw materials, important intermediates in the pharmaceutical industry and fragrance manufacturing industry [1] . For example, p-hydroxyacetophenone can be used in the synthesis of pharmaceutical intermediates and feed additives, such as choleretic and anti-asthma drug salbutamol (Salbutamol), anti-inflammatory drug butyl hydroxy acid (Bufexamac), etc.; Ketones are mainly used as pharmaceutical intermediates and synthetic spices, such as Class IA antiarrhythmic drug Propafenone Hydrochloride, antifungal drug Croconazole Hydrochloride, etc. Because of its wide application, it is parti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/54C07C49/825
CPCC07C45/54C07C49/825
Inventor 王爱玲张腾崔颖娜郑学仿张殊佳张晓辉李德鹏
Owner DALIAN UNIV
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