Hydrochloric Acid → Cinnamoylbenzene

Participants

Reaction Steps

To a solution of acetophenone (0.05 mol) and aldehyde (0.05 mol) in 150 ml of MeOH was added 2.5 eq of NaOH as pellets. The reaction bottle was placed on a shaker (slightly exothermic reaction) for 24-48 hrs. Then the reaction container was placed in an acetone-ice bath (−5 to 0° C.) and the reaction mixture was quenched with 10.3 ml of 37% aqueous HCl (2.5 eq). Solvent was removed in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was discarded and the organic layer was washed with water, brine and dried over Na2SO4. Solvent was removed in vacuo and the crude chalcone (compound 1) was recrystallized from methanol (MeOH) or a mixture of hexane and ethyl acetate (Hex:EtOAc) 3:1 or purified by silica gel chromatography using a mixture of Hex:EtOAc=5:1 as an eluent.

Provenance & Evidence