Water → 1-[4-(Benzyloxy)phenyl]ethan-1-one

Participants

Reaction Steps

To a solution of 13.6 g (100.0 mmol) of 4-hydroxyacetophenone in 100 mL of DMF was added 20 g (144 mmol) of K2CO3, then 12 mL (101 mmol) of benzyl bromide. The reaction was stirred for 1.5 h at ambient temperature, then poured into 300 mL of H2O to give a white precipitate. This was filtered and washed with 50 mL of H2O. The product was taken up in 100 mL of CH2Cl2, and the H2O that separated was drained. The organic layer was extracted with H2O (1×25 mL) and brine (1×25 mL), dried over MgSO4, filtered, and concentrated to 22.1 g (98%) of a white solid as the titled compound. MS (ESI) m/e 226.9, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 2.50 (m, 3H) 5.21 (s, 2H) 7.11 (m, 2H) 7.41 (m, 5H) 7.92 (m, 2H).

Provenance & Evidence