Toluene → 4-Phenyl-2,3-dihydro-1H-inden-2-ol

Participants

Reaction Steps

A solution of the 79.6 g of oil and 0.1 g of p-toluene-sulfonic acid in 350 ml of toluene was heated at reflux for 15-20 minutes during which a toluene/water azeotrope collected in a Dean-Stark trap. The mixture was cooled, placed on a silica gel chromatography column, and eluted first with toluene, then with 1:1 toluene/ethyl acetate. Appropriate fractions were combined and concentrated to give, after crystallization from toluene, 44.5 g of 4-phenyl-2-indanol, mp 71°-73° C. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence