Phenol oxidation. The formation of benzofuran and 2,3-dihydrobenzofuran derivatives by oxidation of 1-(2-hydroxyphenyl)-2-(4-hydroxyphenyl)ethanes

Abstract

Oxidation of 1-(2-hydroxyphenyl)-2-(4-hydroxyphenyl)ethane with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) gives a mixture of 2-(4-hydroxyphenyl)benzo[b]furan and 2,3-dihydro-2-(4-hydroxyphenyl)benzo[b]-furan in proportions dependent upon the amount of DDQ used. An alternative synthesis of one of the products is reported. Oxidations of 1-(2-hydroxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)ethane with DDQ and with alkaline potassium ferricyanide are also described.