4'-Hydroxypropiophenone → 1-Propanone, 1-(4-(2-propenyloxy)phenyl)- (9CI)

Participants

Reaction Steps

To 1-(4-hydroxy-phenyl)-propan-1-one (4.6 g, 30 mmol) and K2CO3 (5 g, 36 mmol) in DMF (10 mL) was added allylbromide (7.26 g, 60 mmol) dropwise with violent stirring. The reaction mixture was stirred at room temperature for 12 h and filtered to remove salt. The filtrate was concentrated to yield the titled compound (5.5 g, 97%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.94 (d, 2H, J=9.0 Hz), 7.05 (d, 2H, J=9.0 Hz), 6.05 (m, 1H), 5.44, 5.38, 5.30, 5.26 (4d, 2H, J=3.0 Hz), 4.66 (d, 2H, J=6.0 Hz), 2.98 (q, 2H, J=7.5 Hz), 1.07 (t, 3H, J=7.5 Hz). MS (ESI) m/e 191 (M+H)+; 189 (M−H)−.

Provenance & Evidence