BENZYL ALCOHOL (Phenyl Carbinol), C6H5CH2OH, occurs as a benzoic ester in Peru balsam, as cinnamic ester in Tolu balsam, as acetic ester in essential oil of jasmine, and also in storax. It may be synthetically prepared by the reduction of benzoyl chloride; by the action of nitrous acid on benzylamine; by boiling benzyl chloride with an aqueous solution of potassium carbonate, or by the so-called "Cannizzaro" reaction, in which benzaldehyde is shaken up with caustic potash, one half of the aldehyde being oxidized to benzoic acid, and the other half reduced to the alcohol. (Berichte, 1881, 14, p. 2394).
2C6H5CHO + KOH = C6H5COOK + C6H5CH2OH.
It is a colourless liquid, with a faint aromatic smell, and boils at 206° C. On oxidation with nitric acid it is converted into benzaldehyde, whilst chromic acid oxidizes it to benzoic acid. Reduction by means of hydriodic acid and phosphorus at 140° C. gives toluene, whilst on distillation with alcoholic potash, toluene and benzoic acid are formed.
Note - this article incorporates content from Encyclopaedia Britannica, Eleventh Edition, (1910-1911)