Intramolecular catalysis in the oxidation of 2-carboxybenzaldehyde with bromine

Abstract

It is shown that the rate of oxidation in aqueous solution with bromine of the anion of 2-carboxybenzaldehyde is 70 times that of benzaldehyde, this being attributed to intramolecular general base catalysis of the oxidation by the neighbouring carboxylate group. Together with the observation of general base catalysis in the oxidation of benzaldehyde, these results confirm a previous suggestion that the aldehyde hydrate is the reactive entity in the bromine oxidation of both aromatic and aliphatic aldehydes in aqueous solution.