Preparation method of 2-hydroxyacetophenone

A technology of o-hydroxyacetophenone and phenol, applied in the field of preparation of o-hydroxyacetophenone and o-hydroxyacetophenone, can solve the problems of low yield, complicated preparation method and process, and achieves high yield, low cost, The effect of low cost of raw materials

Inactive Publication Date: 2015-12-09
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a kind of preparation method of o-hydroxyacetophenone, the preparation method of described this o-hydroxyacetophenone solves the complex process of the preparation method in the prior art, Technical problem with low yield

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  • Preparation method of 2-hydroxyacetophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0032] 1) Preparation of phenol acetate

[0033] Add 14.1g (0.15mol) of phenol, 14.13g (0.18mol) of acetyl chloride, and 40ml of cyclohexane into a three-neck flask, and react at room temperature for 2-3 hours. After the plate reaction is completed, adjust the pH to about 8 with sodium bicarbonate solution. The organic phase was collected and dried over anhydrous sodium sulfate to obtain 20.2 g of the product light yellow oily liquid phenol acetate (yield 99%).

[0034] 2) the preparation of o-hydroxyacetophenone

[0035] a. Add 13.6g (0.1mol) of phenol acetate in a three-necked flask, add 16g (0.12mol) of aluminum trichloride, heat and reflux at 120°C for 1.5h, after the plate reaction is completed, add 50ml of mass fraction of 5% hydrochloric acid solution, extracted 3 times with ethyl acetate, collected the organic phase, extracted with the second organic solvent; concentrated the organic layer, added 1-2 times the volume of the third organic solvent, the organic layer was...

Embodiment 2

[0040] 1) Preparation of phenol acetate

[0041] Add 14.1g (0.15mol) of phenol, 14.13g (0.18mol) of acetyl chloride, and 240ml of chloroform into a three-neck flask, and react at room temperature for 2-3 hours. After the plate reaction is completed, adjust the pH to about 8 with sodium bicarbonate solution. Collect the organic phase and dry it over anhydrous sodium sulfate to obtain 12.05 g of product light yellow oily liquid phenol acetate (yield 59%)

[0042] 2) the preparation of o-hydroxyacetophenone

[0043] a. Add 13.61g (0.1mol) of phenol acetate to a three-necked flask, add 16g (0.12mol) of aluminum trichloride, heat and reflux at 130°C for 1.5h, after the plate reaction is complete, add 50ml of mass fraction to 5 % hydrochloric acid solution, extracted 3 times with ethyl acetate, concentrated the organic layer, added 1-2 times the volume of the third organic solvent, the organic layer was frozen and filtered, and the operation was repeated 2-3 times to obtain the fil...

Embodiment 3

[0047] 1) Preparation of phenol acetate

[0048] Add 14.1g (0.15mol) of phenol, 14.13g (0.18mol) of acetyl chloride, and 40ml of toluene into a three-necked flask, and react at room temperature for 2-3h. After the plate reaction is completed, adjust the pH to about 8 with sodium bicarbonate solution. Collect the organic phase and dry it over anhydrous sodium sulfate to obtain 17.77 g (yield 87%) of product light yellow oily liquid phenol acetate

[0049] 2) the preparation of o-hydroxyacetophenone

[0050] a. Add 13.6 g (0.1 mol) of phenol acetate in a three-necked flask, add 16 g (0.12 mol) of aluminum trichloride, heat and reflux at 140 ° C for 1.5 h, and after the plate reaction is complete, add 50 ml with a mass fraction of 5% hydrochloric acid solution, extract 3 times with ethyl acetate, concentrate the organic layer, add 1-2 times the volume of the third organic solvent, freeze the organic layer, filter, repeat the operation 2-3 times, the obtained filter cake, The pr...

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Abstract

The invention discloses a preparation method of 2-hydroxyacetophenone. The preparation method comprises the steps: weighing phenol and acetyl chloride with the molar ratio of phenol to acetyl chloride of 1 to (1.0-1.5), adding phenol and acetyl chloride to a first organic solvent for reaction, carrying out a reaction at the temperature of 20-30 DEG C, then washing with a weak base, and drying and spin-drying to obtain phenyl acetate; adding Lewis acid and an ionic liquid in phenol acetate, wherein the mass of the ionic liquid is 3-10 times that of phenyl acetate, and the reaction temperature is 120-160 DEG C; hydrolyzing the obtained product with a hydrochloric acid solution, and extracting with a second organic solvent; and concentrating an organic layer, then adding a third organic solvent with the volume 1-2 times that of the organic layer, freezing the organic layer, filtering, repeating the operations for 2-3 times, and distilling the obtained filter cake to obtain the product 2-hydroxyacetophenone. The adopted raw materials are low in price, the experimental conditions are mild, the yield is high, the ortho-para ratio can reach 3.55:1, and the preparation method has a great application value in production.

Description

technical field [0001] The invention belongs to the field of chemical industry, relates to a kind of o-hydroxyacetophenone, specifically a kind of preparation method of o-hydroxyacetophenone. Background technique [0002] O-hydroxyacetophenone is an important pharmaceutical and fine chemical intermediate, such as a raw material for the synthesis of chalcones. However, chalcone compounds have a wide range of biological activities due to their greater flexibility in molecular structure and the ability to bind to different receptors. (Dang Shan, Liu Jingui, Wang Guohui, Synthetic Chemistry. Synthesis of 2-Hydroxychalcone at room temperature. 2008 (4). 460-463) Flavonoids are non-toxic and harmless, and have the functions of scavenging free radicals, anti-oxidation, anti-cancer, Antibacterial, anti-allergic, anti-inflammatory, anti-viral and other biological activities and pharmacological effects are of great significance to the treatment and prevention of human tumors, aging, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/825C07C45/54
CPCC07C45/54C07C67/14C07C49/825C07C69/14
Inventor 林淑慧刘维俊胡艳
Owner SHANGHAI INST OF TECH
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