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Method for synthesizing trifluoromethoxybenzene

A technology of trifluoromethoxybenzene and methoxyaniline, which is applied in the field of synthesis of trifluoromethoxybenzene, can solve problems such as inability to realize large-scale industrial production and incomplete reaction of trifluoromethoxybenzene, and achieve Effect of reduced reaction cost, high purity, and high specific surface area

Inactive Publication Date: 2011-05-18
TIANJIN TIANCHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the incomplete reaction of existing trifluoromethoxybenzene, the need for high-vacuum distillation, the shortcomings and shortcomings that cannot be realized in large-scale industrial production, and provide an economical, convenient and suitable for industrial production of trifluoromethoxybenzene Preparation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Under the protection of nitrogen, 2 kg of methyl 5,5,5-trifluoro-4-oxovalerate, 2 g of 10% palladium-carbon, 1 L of toluene, and 2 kg of 2-methyl-4-methoxyaniline were added. At 40°C, pressurize at 25 atm, and stir for 20 hours. After the hydrogen absorption is completed, filter and concentrate the filtrate to dryness. 85% ethanol was added to the residue, concentrated hydrochloric acid was added dropwise, and a large amount of crystals were precipitated. Heat to reflux for 30 minutes. Cool at 0°C, filter, and separate the crude product by silica gel column technology to finally obtain the target compound trifluoromethoxybenzene as light yellow liquid. Dry until the water content is ≤0.5%, and white crystals are obtained.

Embodiment 2

[0020] Under the protection of nitrogen, with benzene or toluene as solvent, add a certain amount of 5,5,5-trifluoro-4-carbonylvaleric acid methyl ester 2kg and 2-methyl-4-methoxyaniline 4kg in the reaction vessel ; 4 grams of 10% palladium-carbon, the catalyst participated in the reaction, heated to reflux for 24 hours, while constantly stirring to make the reaction complete; after the reaction was completed, the solvent was evaporated under reduced pressure; the crude product was separated by silica gel column technology, and the solvent was dehydrated alcohol or 95% ethanol. Finally, the target compound trifluoromethoxybenzene was obtained as light yellow liquid.

Embodiment 3

[0022] Under nitrogen protection, using benzene or toluene as a solvent, add a certain amount of 5,5,5-trifluoro-4-carbonyl pentanoic acid methyl ester 2.5kg and 2-methyl-4-methoxyaniline into the reaction vessel 4.8kg; 2.5 grams of 10% palladium-carbon, the catalyst participated in the reaction, heated to reflux for 18 hours, while constantly stirring to make the reaction complete; after the reaction, the solvent was evaporated under reduced pressure; the thick product was separated by silica gel column technology, and the solvent was water ethanol or 80% ethanol. Finally, the target compound trifluoromethoxybenzene was obtained as light yellow liquid.

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Abstract

The invention relates to a new method for synthesizing trifluoromethoxybenzene, which comprises the following steps of: under the protection of nitrogen, adding a certain amount of 5,5,5-trifluoro-4-oxopentanoate and 2-methyl-4-methoxybenzenamine into a reaction container by taking benzene or methylbenzene as a solvent; reacting in the presence of a catalyst, heating and refluxing for 24 hours, and constantly stirring for complete reaction; after reaction, steaming to remove the solvent under reduced pressure; separating a crude product by using silica gel column chromatography; and finally obtaining a light yellow liquid target compound, namely 5,5,5-trifluoro-4-(2-methyl-4-methoxybenze-imido)methyl pentanoate. The method has the advantages that: raw materials are readily available; the process is simple; and the product is prepared by a two-step method, so the method is stable and reliable, and the production efficiency is high.

Description

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Claims

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Application Information

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IPC IPC(8): C07C43/225C07C41/01
Inventor 张国基
Owner TIANJIN TIANCHENG PHARMA
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