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Method for synthesizing benzyl cyanide compound by using benzyl chloride compound

A compound, the technology of phenylacetonitrile, which is applied in the field of synthesis of phenylacetonitrile compounds, can solve the problems of high industrial application cost and high toxicity of cyanide reagents, and achieve the effects of low toxicity, low price and reduced production cost

Inactive Publication Date: 2012-03-21
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

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Experimental program
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Effect test

Embodiment 1

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

Embodiment 2

[0029] Add 0.3mmol cuprous iodide and 0.3mL toluene solvent into the reaction tube, stir for 1 minute; then add 0.5mmol K 4 [Fe(CN) 6 ], 1 mmol o-methylbenzyl chloride and 0.7 mL toluene. After sealing the reaction tube, it was stirred at 180° C. for 20 h. After the reaction system was cooled to room temperature, 1 mL of acetophenone in dichloromethane (0.8 mmol / mL) was added as an internal standard, stirred evenly and left for more than 1 hour, and the supernatant was analyzed by gas chromatography. The yield is 82%. O-tolueneacetonitrile (C 9 h 9 N) mass spectrum 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 cuprous iodide and 0.3mL toluene solvent into the reaction tube, stir for 1 minute; then add 0.5mmol K 4 [Fe(CN) 6 ], 1 mmol m-methylbenzyl chloride and 0.7 mL toluene. After sealing the reaction tube, it was stirred at 180° C. for 20 h. After the reaction system was cooled to room temperature, 1 mL of acetophenone in dichloromethane (0.8 mmol / mL) was added as an internal standard, stirred evenly and left for more than 1 hour, and the supernatant was analyzed by gas chromatography. The yield is 76%. m-tolueneacetonitrile (C 9 h 9 N) Mass spectrum, molecular ion peak (M+) theoretical value 131.07, measured value 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 Applications(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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