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 Preparation of Allyl cyanide
  • Preparation of Allyl cyanide
  • Allyl (CAS NO.: ), which is also known as 3-Butenenitrile, could be produced through the following synthetic routes.

    Preparation of Allyl cyanide

    (A) Preparation of Cuprous Cyanide.—In a 6-l. round-bottomed flask fitted with a stopper carrying a mechanical stirrer, a separatory funnel, and a gas exit tube leading to a good hood, is placed a solution of 650 g. (2.6 moles) of crystallized copper sulfate in 4 l. of water. The flask is surrounded by an oil bath and heated to about 80°. The stirrer is started and a solution of 255 g. (5.2 moles) of sodium cyanide in 650 cc. of water is added from the separatory funnel over a period of about one-half hour. Then the mixture is boiled until no more cyanogen gas is evolved. This requires about five to ten minutes.

    The cuprous cyanide, which begins to separate as a light tan precipitate as soon as any of the cyanide solution is added, is allowed to settle and the solution is decanted. The precipitate is filtered, then washed with water (1 l.) and finally with alcohol (500 cc.) and ether (300 cc.). After drying at 110° for about thirty-six hours, the product weighs 200–210 g. (85–90 per cent of the theoretical amount).

    (B) Allyl Cyanide (CAS NO.: ).—In a 1-l. round-bottomed flask fitted with a condenser and a mechanical stirrer are placed 220 g. (1.83 moles) of allyl bromide and 170 g. (1.9 moles) of dry cuprous cyanide. The mixture is heated in a water bath and the stirrer rotated slowly by hand until the reaction starts (about fifteen to thirty minutes). When the reaction once begins, it becomes vigorous, and the heating bath must be replaced by a cooling mixture of ice and water in order to avoid loss of product through the condenser. After the vigorous reaction has subsided, the water bath is replaced, the mechanical stirrer is started and the mixture is heated until no more allyl bromide refluxes. This requires about one hour.

    The condenser is then set for distillation and the allyl cyanide is distilled from the flask by heating it in an oil bath with stirring. Upon redistillation, the allyl cyanide is pure and boils at 116–121° with almost no loss. The yield is 98–103 g. (80–84 per cent of the theoretical amount).


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