4'-Hydroxyacetophenone → 4'-Hydroxy-3,4-methylenedioxy-chalcone

Participants

Reaction Steps

4-Hydroxy acetophenone, 1 (2.7 g, 20 mmol), 3,4-methylenedioxy benzaldehyde, 6 (3 g, 20 mmol) and 50% aqueous sodium hydroxide (5 mL) in methanol (40 mL) were reacted under reflux as in 7 to yield 11. Yield 3.5 g (65%); mp 191-193° C.; MS (FAB) 269 (M++1); IR (KBr) 3410, 1646; 1H NMR (200 MHz, CDCl3) δ 9.15 (s, 1H), 7.98 (d, J=8.7 Hz, 2H), 7.72 (d, J=15.5 Hz, 1H), 7.37 (d, J=15.5 Hz, 1H), 7.16 (s, 1H), 7.12 (d, J=8.1 Hz, 1H), 6.99 (d, J=8.8 Hz, 2H), 6.82 (d, J=7.9 Hz, 1H), 6.02 (s, 2H).

Provenance & Evidence