Synthesis of 9-Anthryl Ethers from trans-9,10-Dihydro-9,10-dimethoxy­anthracene by Acid-Catalyzed Transetherification

Abstract

During a study of electrophilic aromatic addition reactions (Ad E Ar) to anthracene, anthryl ethers at the C9-position of anthracene were obtained as the major products when trans-9,10-dihydro-9,10-dimethoxyanthracene was reacted (10 minutes at 75°C) with various alcohols. 9-Anthryl ethers with primary, secondary, cyclic alcohols, and polyethylene glycol (PEG) were isolated in 47-73% yields under optimized conditions. It is hoped that the devised method offers a new synthetic route for the preparation of anthryl ethers via the acid-catalyzed transetherification of trans-9,10-dihydro-9,10-dimethoxyanthracene with various alcohols.