One-step novel synthesis of methylene bisphenols and methylene bisnaphthols using Lewis acid mediated rearrangement

Mono- and di-substituted isomeric methylene bisphenols and methylene bisnaphthols have been synthesized by rearrangement of the corresponding O-methoxyacetyl derivatives of phenols and naphthols, respectively, in presence of aluminium chloride under dry conditions. The chemistry observed is different from the usual Fries rearrangement reaction and involves an intermolecular rearrangement. The reactions reported here also reflect the influence of substituents present in the substrate as is supported by the substitution of the bridging methylene at a position meta to the phenolic hydroxyl in some of the minor products formed along-side the majorly formed ortho substituted products.