4'-Hydroxyacetophenone → 3,4-Dimethoxy-4'-hydroxychalcone

Participants

Reaction Steps

4-Hydroxy acetophenone, 1 (13.6 g, 100 mmol), 3,4-dimethoxy benzaldehyde, 5 (16.6 g, 100 mmol) and 50% aqueous sodium hydroxide (80 mL) in methanol (200 mL) were reacted under reflux as in 7 to yield 10. Yield 19.6 g (69%); mp 193-195° C.; MS (FAB) 285 (M++1); IR (KBr) 3443, 1643; 1H NMR (200 MHz, CDCl3) δ 10.45 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.81 (d, J=15.5 Hz, 1H), 7.66 (d, J=15.5 Hz, 1H), 7.52 (s, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 6.93 (d, J=8.5 Hz, 2H), 3.95 (s, 3H), 3.92 (s, 3H).

Provenance & Evidence