Abstract
This chapter presents physical properties, synthesis, and methods of analysis of benzyl benzoate. It is a colorless oily liquid and has a pleasant aromatic odor and sharp burning taste. It is insoluble in water or glycerol, miscible with alcohol (95%), chloroform, ether, oils, acetone, benzene, methanol, and petroleum ether. In the experiments described in the chapter, the infrared spectrum of benzyl benzoate was recorded as a film on a Unicam SP 3–300 spectrophotometer. The ultraviolet (UV) spectrum of benzyl benzoate in ethanol was scanned from 400–200 nm using Varian Cary 219, and six maxima and six minima were observed. The chapter discusses proton nuclear magnetic resonance (NMR) spectra of benzyl benzoate in deuterated chloroform and in dimethyl sulfoxide–D6 (DMSO-D6). Three main methods were used for preparation of benzyl benzoate: (1) esterification of benzoic acid with benzylalcohol, (2) transposition between sodium benzoate and benzylchloride, and (3) condensation of two molecules of benzaldehyde in the presence of sodium hydroxide. Benzyl benzoate is rapidly hydrolyzed in vivo to benzoic acid and benzylalcohol. Benzylalcohol in turn is oxidized to benzoic acid, which is then conjugated with glycine to form hippuric acid.
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