2',4'-Dihydroxyacetophenone → 4'-Benzyloxy-2'-hydroxyacetophenone

Participants

Reaction Steps

Potassium carbonate (27.2 g, 0.2 mol) followed by benzyl bromide (7.04 mL, 59.2 mmol) were added to a solution of 1-(2,4-dihydroxy-phenyl)-ethanone (10 g, 66 mmol) in DMF (90 mL). The mixture was stirred for 2 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) followed by recrystallization gave the title compound as a white solid (8.7 g, 55%). 1H NMR (400 MHz, CDCl3): δ 2.55 (s, 3H), 5.09 (s, 2H), 6.50 (s, 1H), 6.51 (dd, J=9.1, 3.9 Hz, 1H), 7.34-7.43 (m, 5H), 7.64 (d, J=9.1 Hz, 1H), 12.73 (s, 1H).

Provenance & Evidence