Sulfuric Acid → 4-(Oxan-4-yl)phenol

Participants

Reaction Conditions

Reaction Steps

A solution of 5.2 g of sodium nitrite in 10 ml of water was added to a mixture of 13 g of 4-(p-aminophenyl)-tetrahydropyran and 100 ml of concentrated sulfuric acid cooled to 5° C and the mixture was stirred at 5° C for 30 minutes. The mixture was poured into a solution of 100 ml of water and 10 ml of concentrated sulfuric acid heated to 75°-80° C and the mixture was held at 75°-80° C for 15 minutes and was then cooled to 4° C. The mixture was filtered and the recovered crystals were washed with water and dried to obtain 12.7 g of 4-(p-hydroxyphenyl)-tetrahydropyran melting at 164° C.

Provenance & Evidence