(CAS NO.: ), which is also known as Glyoxylonitrile, phenyl-, could be produced through the following synthetic routes.

In a 500-ml. distilling flask fitted with a thermometer extending to within 0.5 in. of the bottom are placed 110 g. (1.2 moles) of cuprous cyanide and 143 g. (118 ml., 1.02 moles) of purified benzoyl chloride. The flask is shaken to moisten almost all the cuprous cyanide and is placed in an oil bath which has been previously heated to 145–150°. The temperature of the bath is raised to 220–230° and maintained between these limits for 1.5 hours. During the heating the flask is frequently removed from the bath (about every 15 minutes) and the contents are thoroughly mixed by vigorous shaking. At the end of the 1.5 hours the flask is connected with an air-cooled condenser set for downward distillation. The temperature of the bath is slowly raised to 305–310°, and distillation is continued until no more product comes over. About 100–112 g. of crude benzoyl cyanide boiling at 207–218°/745 mm. is obtained.

The crude benzoyl cyanide is purified by fractional distillation through a column. The low-boiling material is taken off at a reflux ratio of 25–30 to 1 until the temperature reaches 208°; about 15 g. is collected. The benzoyl cyanide is collected at a reflux ratio of 1 to 1 at a temperature of 208–209°/745 mm. (bath temperature 260–280°). The distillate solidifies to colorless crystals which melt at 32–33°; the product weighs 80–86 g. (60–65%).