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ChemicalBook CAS DataBase List Benzoyl cyanide

Benzoyl cyanide synthesis

12synthesis methods
Benzoyl cyanide is prepared by treatment of benzoyl chloride with sodium cyanide under phase-transfer catalytic conditions. This process is also used to convert 4-methyl, 4-methoxy, and 4-chlorobenzoyl chlorides into the corresponding benzoyl cyanides, and similarly cinnamoyl chloride into cinnamoyl cyanide (98%).
Preparation of Benzoyl cyanide
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Yield:613-90-1 93%

Reaction Conditions:

with oxalyl dichloride;Triphenylphosphine oxide in ethyl acetate at 20; for 1 h;

Steps:

4.3.1. Method a
General procedure: To a solution of triphenylphosphine oxide (14 mg, 0.050 mmol) in either CHCl3, CDCl3 or EtOAc (2.0 mL) was added oxalyl chloride (102 μL, 1.21 mmol) and the reaction mixture was stirred for 5 min. The appropriate oxime (1.00 equiv) as solution in either CHCl3, CDCl3 or EtOAc (1.0 mL) was then added over 0.5 h via syringe pump at room temperature and the reaction mixture was stirred for a further 0.5 h at room temperature after which the solvent was removed in vacuo. Purification by flash chromatography (silica, 10-100% Et2O/pet. ether) gave the pure nitriles.

References:

Denton, Ross M.;An, Jie;Lindovska, Petra;Lewis, William [Tetrahedron,2012,vol. 68,# 13,p. 2899 - 2905] Location in patent:supporting information; experimental part

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