Water → HCID 9817035, compound

Participants

Reaction Steps

A solution of acetic anhydride (3.27, 0.032 mol) in pyridine (50 mL) was stirred at 0°. 2-Phenylmethyl-1-naphthol (5.00 g, 0.021 mol) was added and the mixture was stirred while warming to room temperature. After 18 h, water was added and the mixture was extracted with ether. The ether phase was washed with dilute hydrochloric acid, then with water, then with brine and was dried over MgSO4. Concentration afforded a brown oil which was flash chromatographed (5% ethyl acetate/hexane). The resulting oil crystallized on standing and was recrystallized (hexane) to provide the title compound (4.75 g, 82%) as white needles: mp 67°-69°; NMR (CDCl3) 7.9-7.6 (m, 3H), 7.45 (m, 2H), 7.20 (m, 6H), 4.01 (s, 2H), 2.40 (s, 3H); IR (mull) 1760; Mass Spec (EI) 276 (9), 234 (100), 156 (20); Calcd. for C19H16O2;C-82.57 H-5.84., Found: C-82.66 H-5.93

Provenance & Evidence