BENZALDEHYDE

(C6H5CHO), the simplest representative of the aromatic aldehydes, occurring naturally as the glycoside amygdalin. Prepared synthetically, it is used chiefly in the synthesis of other organic compounds and to some extent in perfumes and flavouring agents. Benzaldehyde was first isolated in 1803, and in the 1830s the German chemists Justus von Liebig and Friedrich Whler investigated the compound in studies that laid the foundation for the structural theory of organic chemistry. Industrially, benzaldehyde is made by processes in which toluene is first chlorinated to benzyl chloride or to benzal chloride. Direct oxidation of toluene with manganese dioxide also produces benzaldehyde. Benzaldehyde is readily oxidized to benzoic acid and is converted to addition products by hydrocyanic acid or sodium bisulfite. It undergoes simultaneous oxidation and reduction with alcoholic potassium hydroxide, giving potassium benzoate and benzyl alcohol; with alcoholic potassium cyanide, it is converted to benzoin; with anhydrous sodium acetate and acetic anhydride, it gives cinnamic acid.