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Method for synthesizing benzyl cyanide compound by using benzyl chloride compound

A compound, phenylacetonitrile technology, applied in the field of phenylacetonitrile compound synthesis, can solve the problems of high industrial application cost, high toxicity of cyanating reagents, etc., and achieve the effects of low toxicity, low price, and reduced production cost

Inactive Publication Date: 2014-03-26
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The object of the present invention is to provide a kind of method for synthesizing benzyl nitrile compound by benzyl chloride compound, overcome the problem that cyanide reagent toxicity is big or industrial application cost is high in the existing method

Method used

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  • Method for synthesizing benzyl cyanide compound by using benzyl chloride compound
  • Method for synthesizing benzyl cyanide compound by using benzyl chloride compound
  • Method for synthesizing benzyl cyanide compound by using benzyl chloride compound

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add 0.3mmol of cuprous iodide and 0.3mL of toluene solvent into the reaction tube, stir for 1 minute; then add 0.5mmol of K 4 [Fe(CN) 6 ], 1mmol benzyl chloride and 0.7mL toluene. After sealing the reaction tube, it was stirred at 180°C for 20 h. After the reaction system is cooled to room temperature, add 1mL of acetophenone in dichloromethane solution (0.8mmol / mL) as the internal standard, stir well and let stand for more than 1 hour, take the supernatant and analyze by gas chromatography, the yield of benzyl cyanide 78%, benzyl acetonitrile (C 8 H 7 N) Mass spectrometry such as figure 1 As shown, the theoretical value of the molecular ion peak (M+) is 117.06, and the measured value is 117.1.

Embodiment 2

[0029] Add 0.3mmol of cuprous iodide and 0.3mL of toluene solvent into the reaction tube, stir for 1 minute; then add 0.5mmol of K 4 [Fe(CN) 6 ], 1mmol o-methylbenzyl chloride and 0.7mL toluene. After sealing the reaction tube, it was stirred at 180°C for 20 h. After the reaction system is cooled to room temperature, add 1mL of acetophenone in dichloromethane solution (0.8mmol / mL) as the internal standard, stir well and let stand for more than 1 hour, take the supernatant for gas chromatography analysis, o-methylbenzeneacetonitrile The yield was 82%. O-Toluene acetonitrile (C 9 H 9 N) Mass spectrometry such as figure 2 As shown, the theoretical value of the molecular ion peak (M+) is 131.07, and the measured value is 131.1.

Embodiment 3

[0031] Add 0.3mmol of cuprous iodide and 0.3mL of toluene solvent into the reaction tube, stir for 1 minute; then add 0.5mmol of K 4 [Fe(CN) 6 ], 1mmol m-methylbenzyl chloride and 0.7mL toluene. After sealing the reaction tube, it was stirred at 180°C for 20 h. After the reaction system is cooled to room temperature, add 1mL of acetophenone in dichloromethane solution (0.8mmol / mL) as the internal standard, stir well and let stand for more than 1 hour, take the supernatant for gas chromatography analysis, m-methylbenzene acetonitrile The yield was 76%. M-methylbenzene acetonitrile (C 9 H 9 N) Mass spectrum, the theoretical value of the molecular ion peak (M+) is 131.07, and the measured value is 131.1.

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PUM

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Abstract

The invention belongs to the technical field of synthesis of benzyl cyanide compounds and in particular relates to a method for synthesizing a benzyl cyanide compound by using a benzyl chloride compound. The method comprises the following step of: reacting the benzyl chloride compound with potassium ferrocyanide in an organic solvent by using a copper salt as a catalyst to obtain the benzyl cyanide compound. As the less toxic potassium ferrocyanide is used as a cyanide reagent and the inexpensive copper salt is used as the catalyst, the method for synthesizing the benzyl cyanide compound provided by the invention has lower production cost and no highly toxic raw material.

Description

technical field [0001] The invention belongs to the technical field of synthesis of benzyl chloride compounds, in particular to a method for synthesizing benzyl chloride compounds from benzyl chloride compounds. Background technique [0002] Phenylacetonitrile compounds have a wide range of uses, for example, phenylacetonitrile can be used as raw materials for the production of phoxim, daofengsan, penicillin, phenobarbital and kebetidine. The substitution method using benzyl chloride compounds as raw materials is one of the effective methods for producing benzyl cyanide compounds. Based on this method, the technology developed at home and abroad mainly contains: (1) the method (seeing Chidambaram, M.; Sonavane, S. U.; De La Zerda, J.; Sasson, Y. Tetrahedron 2007, 63 , 7696-7701), this method has been widely used in industry, but due to the highly toxic cyanide reagent used, the production protection cost is high; (2) the method using trimethylsilyl cyanide as cyanide reag...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B43/08C07C253/14C07C255/33C07C255/35C07C255/37C07C255/50C07D317/60
Inventor 任运来董传华田欣哲梁菊赵爽王键吉孙艳培
Owner HENAN UNIV OF SCI & TECH
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