Cyclization of a 2-Hydroxymethylchalcone to a phthalan: 1-(2-Hydroxy-4-methoxyphenacyl)-1,3-dihydroisobenzofuran

Abstract

Condensation of 2-acetoxymethylbenzaldehyde with 2-hydroxy-4- methoxyacetophenone gave a low yield of the phthalan named in the title instead of the desired 2-hydroxymethylchalcone. The 1,3- dihydroisobenzofuran, presumably formed by cyclization of the chalcone, showed long-range coupling between the 1- and 3-protons as part of an ABM₂X system.