2'-Hydroxyacetophenone → Cinnamoylbenzene

Participants

Reaction Steps

General procedure for the synthesis of chalcone 32a-l: To a round-bottom flask was charged with 2′-hydroxyacetophenone 31 (1.0 equiv.), 4-allyloxybenzaldehyde (1.0 equiv.) and excess potassium hydroxide solution (3M solution in 96% EtOH). The mixture was stirred at room temperature for 16 h. When TLC indicated complete consumption of 2′-hydroxyacetophenone, the reaction mixture was acidified to pH 5 with 1 M HCl solution at ice-bath temperature. The mixture was continuously extracted with CH2Cl2 (30 mL×3). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure to give a crude mixture, which was washed with 5% ethyl acetate in hexane to furnish desired chalcone.

Provenance & Evidence