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Preparation method of 2-hydroxyl-4-substituted arone compound

A technology for aryl ketones and compounds, which is applied in the field of preparation of 2-hydroxy-4-substituted aryl ketone compounds, can solve the problems of unsuitability for large-scale industrial production, difficulty in product separation and purification, and excessive production of three wastes, etc., and achieve excellent solubility performance , low process pollution and low cost

Active Publication Date: 2015-05-13
BEIJING GREENCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the Fries rearrangement of the process uses the metal catalyst aluminum trichloride, which makes it difficult to separate and purify the product, produces a lot of three wastes, corrodes the equipment, and pollutes the environment. Moreover, the aluminum trichloride explodes when it encounters water during post-reaction treatment, which is dangerous to a certain extent. A small number of times, so it is not suitable for large-scale industrial production

Method used

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  • Preparation method of 2-hydroxyl-4-substituted arone compound
  • Preparation method of 2-hydroxyl-4-substituted arone compound
  • Preparation method of 2-hydroxyl-4-substituted arone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Preparation of 2-hydroxy-4-bromoacetophenone

[0071]

[0072] (1) Preparation of [sulfuric acid][butylammonium triethylamine 4-sulfonate][zinc oxide] ionic liquid

[0073] Under the condition of stirring, slowly drop 9.4g of 1,4-butane sultone into 7.0g of triethylamine, react at 80°C for 2h, cool down to 25°C, filter with suction, wash the filter cake with ethanol three times, Dry in vacuo to obtain triethylamine butane sulfonic acid inner salt.

[0074] Under the ice bath, mix the deionized aqueous solution of 15.8 g of triethylamine butane sulfonic acid inner salt obtained in the previous step and 6.5 g of sulfuric acid, react at 50 ° C for 3 h, and after cooling, vacuum dry to obtain [sulfuric acid] [triethylamine 4-butylammonium sulfonate] ionic liquid intermediate.

[0075] Under stirring conditions, 5.2 g of zinc oxide and 21.3 g of the [sulfuric acid] [triethylamine 4-butylammonium sulfonate] ionic liquid intermediate obtained in the previous step were add...

Embodiment 2

[0083] Preparation of 2-Hydroxy-4-methoxypropiophenone

[0084]

[0085] (1) Preparation of [sulfuric acid][dipropylamine 4-butylammonium sulfonate][copper oxide] ionic liquid

[0086] Under the condition of stirring, slowly drop 21.7g of 1,4-butane sultone into 16.1g of dipropylamine, react at 70°C for 2h, cool down to 25°C, filter with suction, wash the filter cake with ethanol three times, vacuum Dry to obtain dipropylamine butane sulfonic acid inner salt.

[0087] Under an ice bath, mix the deionized aqueous solution of 36.7 g of dipropylamine butane sulfonic acid inner salt obtained in the previous step with 15.2 g of sulfuric acid, react at 60° C. for 5 h, and after cooling, dry in vacuum to obtain [sulfuric acid] [dipropylamine 4- Butylammonium sulfonate] ionic liquid intermediate.

[0088] Under stirring conditions, 11.8 g of copper oxide and 49.7 g of the [sulfuric acid] [dipropylamine 4-butylammonium sulfonate] ionic liquid intermediate obtained in the previous ...

Embodiment 3

[0096] Preparation of 2-Hydroxy-4-methylphenylbenzophenone

[0097]

[0098] (1) Preparation of [sulfuric acid][dipropylamine 4-butylammonium sulfonate][copper oxide] ionic liquid

[0099] Under stirring conditions, slowly drop 14.1 g of 1,4-butane sultone into 10.4 g of dipropylamine, react at 70°C for 2 hours, cool down to 25°C, filter with suction, wash the filter cake with ethanol three times, vacuum Dry to obtain dipropylamine butane sulfonic acid inner salt.

[0100] Under ice bath, mix the deionized aqueous solution of 23.8 g of dipropylamine butane sulfonic acid inner salt obtained in the previous step and 9.8 g of sulfuric acid, react at 60° C. for 5 h, and after cooling, vacuum-dry to obtain [sulfuric acid] [dipropylamine 4- Butylammonium sulfonate] ionic liquid intermediate.

[0101] Under stirring conditions, 7.2 g of copper oxide and 32.2 g of the [sulfuric acid] [dipropylamine 4-butylammonium sulfonate] ionic liquid intermediate obtained in the previous step...

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Abstract

The invention discloses a preparation method of a 2-hydroxyl-4-substituted arone compound. A Bronsted-Lewis dual acidic ionic liquid is taken as a catalyst to catalyze 3-substituted phenolic ester to undergo a Fries rearrangement reaction. The Bronsted-Lewis dual acidic ionic liquid catalyst is a quaternary ammonium salt ionic liquid containing dual acidity, contains a Lewis acid site of copper ions or zinc ions and a Bronsted acid site of a sulfonic group. The Bronsted acid site of the sulfonic group takes the quaternary ammonium salt as a cation and adopts a sulfate radical as an anion. The dual acidic ionic liquid catalyst has strong catalytic activity, high reaction selectivity, and an ortho product with high yield and high purity can be obtained. The reaction aftertreatment is simple and safe, has less pollution, and the catalyst can be used repeatedly. Specifically, the raw material 3-substituted phenolic ester of the Fries rearrangement reaction can be obtained by reaction of 3-substituted phenol with an acylation reagent acyl chloride.

Description

technical field [0001] The invention relates to a method for preparing 2-hydroxy-4-substituted aryl ketone compounds, which belongs to the technical field of organic synthesis. Background technique [0002] Aromatic ketones are important intermediates in the synthesis of fine chemicals, pharmaceuticals, pesticides, and surfactants, among which 2-hydroxy-4-substituent aryl ketones are mainly used in the synthesis of antiarrhythmic drugs - propafenone hydrochloride, sulfonamide anti Intermediates of fungal drugs, anti-allergic diseases and anti-hepatitis C virus drugs. [0003] The method for the synthesis of 2-hydroxyl-4-substituent aryl ketone compounds reported in the literature is to use 3-substituted phenol as a raw material, first carry out an acylation reaction with an acylating agent to obtain a phenolic ester, and then catalyze it under the catalysis of an aluminum trichloride catalyst. Fries rearrangement affords 2-hydroxy-4-substituted aryl ketones. Therefore, the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/825C07C45/51C07C49/84B01J31/26B01J31/28
Inventor 宫宁瑞
Owner BEIJING GREENCHEM TECH
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