Reaction of Benzoic Anhydride with Benzene and Naphthalene in the Presence of Cupric Oxide and Oxygen

Abstract

The reactions of benzoic anhydride with excess benzene and naphthalene in the presence of cupric oxide have been studied under the influence of oxygen.
With benzene, the total yields of phenyl benzoate and phenol produced by the reaction of benzoic anhydride with benzene and by the decomposition of cupric benzoate, increased with increasing initial air pressure, up to the higest value of 26.1 mol% at about 3atm(260 C, 3hrs, cupric oxide/benzoic anhydride=1: molar ratio), and decreased. Similary with naphthalene, the higest yield of β-naphthyl benzoate produced by the reaction of benzoic anhydride with naphthalenewas found to be 13.9mol% at 1atm (250 C).
The results appear to indicate thatthe reaction of copper benzoate with aromatic solvents precedes its intramolecular reaction under the condition where the air pressure. is comparatively low (below 1atm).