The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides

Abstract

The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides is described. On diazotisation, the 2,6-dimethylbenzoate of o-aminophenol is immediately and quantitatively hydrolysed to 2,6-dimethylbenzoic acid and o-hydroxybenzenediazonium chloride. In contrast, the 2,6-dichlorobenzoate of o-aminophenol diazotises normally as do the 2,6-dimethyl-, 4-methoxy-, and 2,6-dimethoxy-benzoates of p-aminophenol. Possible mechanisms for the hydrolytic diazotisation are described.