Intramolecular rearrangement of benzyl benzoate over oxide catalysts. Formation of diphenylmethane and anthrone

Benzyl benzoate undergoes a novel Intramolecular rearrangement over alumina at around 350° C to form O-benzylbenzoic acid which either decarboxylates to diphenylmethane or undergoes cyclodehydration to anthrone. Under the reaction conditions, the anthrone formed undergoes hydrogenation followed by dehydration to anthracene. By carrying out the reactions over modified aluminas. It was demonstrated that better selectivity for Intramolecular rearrangement was obtained on more acidic catalysts. © 1989.