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Method for synthesizing 3-hydroxyacetophenone

A technology of hydroxyacetophenone and acetylbenzenesulfonic acid, which is applied in the field of synthesizing 3-hydroxyacetophenone, can solve the problems of high production cost and expensive raw materials, and achieve the effects of low production cost, short reaction route and easy access

Inactive Publication Date: 2013-11-20
宁波尖锋紫星生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw materials of these methods are relatively expensive, and some will use palladium catalyst, and the production cost is high

Method used

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  • Method for synthesizing 3-hydroxyacetophenone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1) Add 150 ml of 1,2-dichloroethane, 47.5 g (0.36 mol) of aluminum trichloride, and 9.36 g (0.12 mol) of acetyl chloride into a three-necked flask equipped with a mechanical stirrer and a thermometer, and stir well at room temperature Then, 16 g (0.1 mol) of benzenesulfonic acid was added in batches, and after the addition, the temperature was raised to 50° C. and the reaction was continued with stirring for 30 hours. After the reaction was completed, the reaction mixture was slowly poured into 500 ml of ice water, the 1,2-dichloroethane layer was separated, the water layer was extracted twice with 100 ml of 1,2-dichloroethane, and the 1,2-dichloroethane was combined. The ethyl chloride layer was dried over anhydrous sodium sulfate, filtered, and 1,2-dichloroethane was distilled off under reduced pressure to obtain 10 g (0.05 mol) of the product 3-sulfoacetophenone, with a yield of 50%.

[0025] 2) Add 30 g (0.15 mol) of 3-sulfoacetophenone into 200 ml of 5 mol / l potass...

Embodiment 2

[0027] Step (1) is the same as embodiment 1;

[0028] In the step (2), potassium hydroxide was changed to sodium hydroxide, and the others were kept unchanged to obtain 15.3 g (0.11 mol) of solid product 3-hydroxyacetophenone, with a yield of 73%.

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Abstract

The invention discloses a method for synthesizing 3-hydroxyacetophenone. The method comprises the following steps of: adding 1,2-dichloroethane, alchlor and acetylchoride in a reaction container, adding benzenesulfonic acid after evenly stirring, and then heating up to the temperature of 45-55 DEG C to perform stirred reaction for 28-32 hours; after finishing the reaction, slowing pouring ice water in the reaction mixture, layering, extracting the water layer twice with the 1,2-dichloroethane, merging 1,2-dichloroethane layers, drying, filtering, distilling at reduced pressure, and then obtaining 3-acetyl benzenesulfonic acid; adding the 3-acetyl benzenesulfonic acid in alkaline solution, heating so as to dissolve the 3-acetyl benzenesulfonic acid, and then continuing the reaction for 28-35 hours at the temperature of 95-105 DEG C; and after finishing the reaction, cooling the reaction mixture to the temperature of 5-10 DEG C, dropwise adding concentrated hydrochloric acid and regulating the PH value to 4.8-5.2, filtering, drying, and then obtaining the 3-hydroxyacetophenone. The method has the advantages of mild reaction conditions, less reaction steps and low cost, and raw materials are cheap and widely available.

Description

technical field [0001] The invention relates to a method for synthesizing 3-hydroxyacetophenone. Background technique [0002] 3-Hydroxyacetophenone, the structural formula is shown in the following formula (1), also known as m-hydroxyacetophenone, m-hydroxyacetophenone, m-acetylphenol, 3-hydroxyacetophenone, 3-acetylphenol, 3-p-hydroxyacetophenone Ketone, benzophenone 3-hydroxyacetate, is mainly used as an intermediate of the drug phenylephrine and is in great demand in the market. [0003] [0004] (1) 3-Hydroxyacetophenone structural formula [0005] The existing method for synthesizing 3-hydroxyacetophenone is to use benzene or benzene derivatives as raw materials, first introduce a protecting group on the 3-hydroxyl group, and then remove the protecting group on the 3-hydroxyl group to obtain it. These protecting groups include methyl [Park, Jiyeon; Chae, Junghyun. Synlett, 2010, 11:1651-1656], benzyl [Zhou, Linna; Wang, Wenjing; et.al., Tetrahedr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/825C07C45/64
Inventor 张华星杨志杰余巍峰陈金虎徐亚萍柴胜利
Owner 宁波尖锋紫星生物科技有限公司