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).