HCID 14519881, compound → 4-Methyl-2-(phenylmethoxy)benzenemethanol

Participants

Reaction Steps

A solution of 4-methyl-2-phenylmethoxy-benzoic acid (30.3 g, 0.125 mol) in 100 ml thionyl chloride containing 3 drops DMF was heated under reflux for 30 min. The SOCl2 was removed under vacuum and the residual oil was diluted with 100 ml dry benzene. The solvent was again removed under vacuum to remove remaining traces of SOCl2 and the crude acid chloride product was added slowly to a solution of NaBH4 (10 g) in dry diglyme (200 ml) at 10°-20° C. The resulting mixture was stirred for 30 min at room temperature and the solvent was removed under vacuum by heating in an oilbath. Water (100 ml) was added slowly to the white solid and then acetic acid (10 ml) was added to ensure complete decomposition of the excess borohydride. The mixture was basified with conc. ammonia and extracted with ethyl acetate to give 4-methyl-2-phenylmethoxybenzenemethanol (26.6 g, 93% crude yield) as an oil.

Provenance & Evidence