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Method for preparing p-benzaldehyde

A technology of trifluoromethylbenzaldehyde and trifluoromethylbenzene is applied in the field of preparation of p-trifluoromethylbenzaldehyde, can solve the problems of harsh reaction conditions, unfriendly environment, and high cost of raw materials, and achieves easy post-processing, The effect of cheap raw materials, process flow and simple operation

Active Publication Date: 2016-03-23
湖南海利常德农药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In summary, it can be seen that because the above synthetic route has factors such as high raw material cost, environmental unfriendliness or harsh reaction conditions, it is necessary to invent a new route to synthesize p-trifluoromethylbenzaldehyde

Method used

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  • Method for preparing p-benzaldehyde

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0028] The preparation of embodiment 1 intermediate 1-nitromethyl-4-trifluoromethylbenzene

[0029] Put 18.0g (0.1mol) of p-chlorobenzotrifluoride and 20.2g (0.2mol) of triethylamine into a 250ml four-neck flask, stir and mix, cool down to -5°C, drop in 30.5g (0.5mol) of nitromethane, drop Bi heat preservation reaction 3h. Add 109.5g (0.3mol) of 10% hydrochloric acid solution after the reaction, extract and separate layers with 100mL toluene, filter, distill to obtain 20.7g1-nitromethyl-4-trifluoromethylbenzene, content 96.9% (liquid chromatography, external standard method).

Embodiment 2

[0030] The preparation of embodiment 2 intermediate 1-nitromethyl-4-trifluoromethylbenzene

[0031] Put 18.0g (0.1mol) of p-chlorobenzotrifluoride and 15.2g (0.15mol) of triethylamine into a 250ml four-neck flask, stir and mix, cool down to -5°C, drop in 12.2g (0.2mol) of nitromethane, drop Bi heat preservation reaction 2h. Add 109.5g (0.3mol) of 10% hydrochloric acid solution after completion of the reaction, extract the layers with 100mL toluene, filter, and distill to obtain 20.6g of 1-nitromethyl-4-trifluoromethylbenzene, with a content of 95.5% (liquid chromatography, external standard method).

Embodiment 3

[0032] The preparation of embodiment 3 intermediate 1-nitromethyl-4-trifluoromethylbenzene

[0033] Put 18.0g (0.1mol) of p-chlorobenzotrifluoride and 10.1g (0.1mol) of triethylamine into a 250ml four-necked flask, stir and mix, cool down to -5°C, drop in 12.2g (0.2mol) of nitromethane, drop Bi heat preservation reaction 2h. Add 109.5g (0.3mol) of 10% hydrochloric acid solution after the reaction, extract the layers with 100mL toluene, filter, and distill to obtain 20.6g of 1-nitromethyl-4-trifluoromethylbenzene, with a content of 95.4% (liquid chromatography, external standard method).

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Abstract

The invention discloses a method for preparing trifluoromethylbenzaldehyde. P-trifluoromethyl chlorobenzene, nitromethane and triethylamine are adopted as initial raw materials, an intermediate 1-nitro methyl-4-benzotrifluoride is prepared through a substitution reaction without a solvent or under the condition that a solvent exists, and then the target product trifluoromethylbenzaldehyde is prepared through an oxidizing reaction under the action of ozone. The mass percentage content of obtained trifluoromethylbenzaldehyde ranges from 98.1% to 99.5% (liquid chromatogram, external standard method), and the total yield ranges from 90.3% to 96.5% (by p-trifluoromethyl chlorobenzene). The reaction equation is shown in the specification. According to the method, the synthetic raw materials and the process routine are improved and innovated, no metal catalyst is adopted any more, the raw materials are cheap and easy to obtain, the process procedure and operation are easy, aftertreatment is easy, a high-quality p-benzaldehyde product can be prepared through two popular reaction steps, namely, the substitution reaction and the ozonation reaction, and the reaction yield and product quality are both high.

Description

technical field [0001] The invention relates to a preparation method of p-trifluoromethylbenzaldehyde. Background technique [0002] p-Trifluoromethylbenzaldehyde is an important pesticide, pharmaceutical intermediate and organic synthesis reagent, which is widely used in many fields. Its molecular structural formula: [0003] [0004] The preparation methods currently reported mainly include: ① Use p-trifluoromethylbenzoyl chloride and p-trifluoromethylbenzonitrile as raw materials and reduce them with hydrogen to obtain p-trifluoromethylbenzaldehyde. ② Use p-trifluoromethylaniline to prepare diazonium salt and then react with formaldehyde oxime to obtain p-trifluoromethylbenzaldehyde. ③Rearrange p-trifluoromethylbenzaldehyde by reacting p-chlorobenzotrifluoride with a sulfonyl reagent. [0005] Patents US5124487, US4500721 ​​and Organic Fluorine Industry, 2011 (4): 48-49 reported that p-trifluoromethylbenzonitrile was used as raw material, under the action of nickel / ...

Claims

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Application Information

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IPC IPC(8): C07C45/40C07C47/55
CPCC07C45/40C07C201/12C07C47/55C07C205/09
Inventor 全春生陈明周勇黄炜刘凤李萍臧阳陵
Owner 湖南海利常德农药化工有限公司
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