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Synthetic method of 4-(2,2-dichloro cyclopropyl)phenol acetate

A technology of dichlorocyclopropylbenzene and dichlorocyclopropyl, which is applied in the field of fine organic chemical synthesis, can solve the problems of cumbersome post-treatment process, poor economy, and increased process cost, so as to improve reaction selectivity and oxidation capacity , Improve the effect of reactivity

Inactive Publication Date: 2018-10-16
XINCHANG COUNTY TAIRU TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this scheme is stable and controllable, and improves the safety of the process, the high price of the above-mentioned acid anhydride also increases the process cost, making the process scheme less economical
[0015] Patent CN103846103A has improved the above-mentioned baeyer-villiger oxidation reaction, using a silica gel-loaded catalyst to catalyze the baeyer-villiger oxidation reaction, but the conversion rate of ketone is only 80-90% when the scheme is implemented, and the post-treatment process is cumbersome

Method used

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  • Synthetic method of 4-(2,2-dichloro cyclopropyl)phenol acetate
  • Synthetic method of 4-(2,2-dichloro cyclopropyl)phenol acetate
  • Synthetic method of 4-(2,2-dichloro cyclopropyl)phenol acetate

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Experimental program
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Effect test

Embodiment 1

[0053] In a dry 500ml four-neck flask equipped with a stirring paddle, a thermometer, and a reflux condenser (the outlet of the condenser is connected to the tail gas absorption system), put into the dried dichloromethane: 250g, anhydrous AlCl 3 : 65g, I 2 : 0.2g. The four-necked flask was cooled externally with a cooling tank refrigerant, and the temperature of the cooling tank refrigerant was set at -20°C. Turn on stirring to lower the temperature, and when the internal temperature reaches -10°C, slowly add 50 g of acetyl chloride (content 98.5%, 0.6274 mol). When the internal temperature reaches -15°C, add 2,2-dichlorocyclopropylbenzene: 79.5 g (content: 98.8%, 0.4200 mol) dropwise into the reaction bottle, and control the dropping time at about 0.5 hours. After the dropwise addition is completed, the internal temperature is -15~-10°C and the reaction is kept for 8 hours. After the heat preservation is completed, 100 ml (temperature: 5-10° C.) of distilled water is added...

Embodiment 2

[0058] In a dry 500ml four-neck flask equipped with a stirring paddle, a thermometer, and a reflux condenser (the outlet of the condenser is connected to the tail gas absorption system), put into the dried dichloromethane: 250g, anhydrous AlCl 3 : 65.7g, ZnI 2 : 0.5g. The four-necked flask was cooled externally with a cooling tank refrigerant, and the temperature of the cooling tank refrigerant was set at -20°C. Turn on stirring to lower the temperature, and when the internal temperature reaches -10°C, slowly add 50 g of acetyl chloride (content 98.5%, 0.6274 mol). When the internal temperature reaches -15°C, add 2,2-dichlorocyclopropylbenzene: 79.4 g (content: 98.8%, 0.4195 mol) dropwise into the reaction bottle, and control the dropping time at about 0.5 hours. After the dropwise addition is completed, the internal temperature is -15~-10°C and the reaction is kept for 8 hours. After the heat preservation is completed, 100 ml (temperature: 5-10° C.) of distilled water is a...

Embodiment 3

[0063] In a dry 500ml four-neck flask equipped with a stirring paddle, a thermometer, and a reflux condenser (the outlet of the condenser is connected to the tail gas absorption system), put into the dried dichloromethane: 250g, anhydrous AlCl 3 : 65g, AlI 3 : 0.5g. The four-necked flask was cooled externally with a cooling tank refrigerant, and the temperature of the cooling tank refrigerant was set at -20°C. Turn on stirring to lower the temperature, and when the internal temperature reaches -10°C, slowly add 50 g of acetyl chloride (content 98.5%, 0.6274 mol). When the internal temperature reaches -15°C, add 2,2-dichlorocyclopropylbenzene: 79.5 g (content: 98.8%, 0.4200 mol) dropwise into the reaction bottle, and control the dropping time at about 0.5 hours. After the dropwise addition is completed, the internal temperature is -15~-10°C and the reaction is kept for 8 hours. After the heat preservation is completed, 100 ml (temperature: 5-10° C.) of distilled water is add...

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Abstract

The invention discloses a synthetic method of 4-(2,2-dichloro cyclopropyl)phenol acetate. The synthetic method comprises the following steps: taking 2,2-dichloro cyclopropyl benzene as a starting rawmaterial and carrying out electrophilic substitution reaction and baeyer-villiger oxidation reaction to synthesize the 4-(2,2-dichloro cyclopropyl)phenol acetate. According to the preparation method disclosed by the invention, an iodine element-containing co-catalyst is added into the electrophilic substitution reaction to reduce the temperature of the electrophilic substitution reaction, so thatthe selectivity of the electrophilic substitution reaction is improved; the content of an ortho-isomer is reduced within 0.3 percent by adopting relatively-inexpensive acetyl chloride as an electrophilic reagent; the activity of oxidation reaction is improved by adding an iron salt catalyst in the baeyer-villiger oxidation reaction, so that the reaction can be successfully carried out under the condition of taking acetic anhydride as an oxidizing medium, the yield of oxidation reaction is improved and potential safety hazards of a post-treatment process are reduced.

Description

technical field [0001] The invention relates to the field of fine organic chemical synthesis, in particular to the synthesis of a pharmaceutical intermediate 4-(2,2-dichlorocyclopropyl)phenol acetate. Background technique [0002] 4-(2,2-dichlorocyclopropyl)phenol acetate, English name [4-(2,2-dichlorocyclopropyl)phenyl]acetate, is an important pharmaceutical intermediate, mainly used in the synthesis of blood lipid-lowering drugs Ciprofibrate. The chemical synthesis reaction of 4-(2,2-dichlorocyclopropyl) phenol acetate is as follows: [0003] 1. Electrophilic substitution reaction: [0004] [0005] 2. 2-Dichlorocyclopropylphenylacetyl chloride 4-(2,2-dichlorocyclopropyl)acetophenone hydrogen chloride [0006] 2. Baeyer-villiger oxidation reaction: [0007] [0008] 4-(2,2-dichlorocyclopropyl)acetophenone hydrogen peroxide 4-(2,2-dichlorocyclopropyl)phenol acetate water [0009] Anhydrous AlCl is generally used in the first step electrophilic substitution reacti...

Claims

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Application Information

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IPC IPC(8): C07C67/16C07C69/65
CPCC07C45/46C07C67/16C07C2601/02C07C49/813
Inventor 赵乐英
Owner XINCHANG COUNTY TAIRU TECH CO LTD
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