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 Synthesis of Benzyl cyanide
  • Synthesis of Benzyl cyanide
  • (CAS no ), which is also known as , phenyl-, could be produced through the following synthetic routes.

    In a 5-l. round-bottomed flask, fitted with a stopper holding a reflux condenser and separatory funnel, are placed 500 g. (10 moles) of powdered sodium cyanide (96–98 per cent pure) and 450 cc. of water. The mixture is warmed on a water bath in order to dissolve most of the sodium cyanide, and then 1 kg. (8 moles) of benzyl chloride (b.p. 170–180°) mixed with 1 kg. of 95 per cent alcohol is run in through the separatory funnel in the course of one-half to three-quarters of an hour. The mixture is then heated under a reflux condenser on the steam bath for four hours, cooled and filtered with suction to remove most of the sodium chloride. It is well to wash the filtered salt with a small portion of alcohol in order to remove any benzyl cyanide which may have been mechanically held.

    The flask is now fitted with a condenser, and as much alcohol as possible is distilled off on the steam bath. The residual liquid is cooled, filtered if necessary, and the layer of benzyl cyanide separated. This crude benzyl cyanide is now placed in a Claisen distilling flask and distilled under reduced pressure, the water and alcohol coming over first, and finally the cyanide. It is advantageous to use a fractionating column or, better still, a Claisen flask with a modified side arm, which gives the same effect as a fractionating column. The material is collected at 135–140° /38 mm. (115–120° /10 mm.). The yield is 740–830 g. (80–90 per cent of the theoretical amount).


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