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

Participants

Reaction Steps

Potassium carbonate (54 g, 0.39 mol) followed by benzyl bromide (13.9 mL, 0.12 mol) were added to a solution of 2′,4′-dihydroxyacetophenone (20 g, 0.13 mol) in DMF (180 mL). The mixture was stirred for 5 hours and then partitioned between H2O and EtOAc. The organic layer was washed with satd NaHCO3, 1N HCl, brine, dried over Na2SO4 and concentrated to a clear oil (23.7 g, 81%). 1H NMR (400 MHz, CDCl3): δ 2.56 (s, 3 H), 5.02 (s, 2 H), 6.51 (m, 2 H), 7.33–7.43 (m, 5 H), 7.64 (d, J=8.3 Hz, 1 H), 12.73 (s, 1 H).

Provenance & Evidence