Benzyl benzoate has been identified in certain natural plant products.[1] In the laboratory it has been prepared by the action of (_a_) benzoyl chloride upon benzyl alcohol,[2] (_b_) benzyl chloride upon sodium benzoate, and (_c_) alcoholates upon benzaldehyde.[3] Recently, Gomberg and Buchler[4] have shown that reaction (_b_) may be conducted even with aqueous solutions of sodium benzoate. [1] Ann. 152, 131 (1869). [2] Gmelin's Handbuch der Organ. Chem. 3, 40. [3] Ber. 20, 649 (1887). Cf. also J. Chem. Soc. 75, 1155 (1899). [4] J. Am Chem. Soc. 42, 2059 (1920). The Claisen method (_c_) furnishes the most convenient and practical procedure for the preparation of this ester. The materials are cheap, the experimental procedure simple, and the product obtained is free from objectionable traces of benzyl chloride. Unfortunately the method has been found to be extremely erratic in regard to yield (10-95 per cent), as well as in regard to purity of the product (87-97 per cent ester).[1] As a result of the present study,[2] causes for variations are fully accounted for and the procedure has been converted into a satisfactory method of preparation. [1] C. A. 14, 3500 (1920). [2] J. Am. Pharm. Assoc. 11, 599 (1922). III BENZYL CYANIDE C6H5CH2Cl + NaCN--> C6H5CH2CN + NaCl Prepared by ROGER ADAMS and A. F. THAL Checked by O. KAMM and A. O. MATTHEWS. 1. Procedure IN a 5-l. round-bottom flask, fitted with a stopper holding a reflux condenser and separatory funnel, are placed 500 g. 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. of benzyl chloride (b. p. 170-180'0) mixed with 1 kg. of 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 with 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 _in vacuo_, 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[1] (Vol. I, p. 40, Fig. 3) which gives the same effect as a fractionating column. The material is collected from 135-140'0/38 mm. (115-120'0/10 mm.). The yield is 740-830 g. (80-90 per cent of the theoretical amount). [1] J. Am. Chem. Soc. 39, 2718 (1917). 2. Notes