Malonic Acid → 3',4'-Dimethoxycinnamic acid

Participants

Reaction Conditions

Reaction Steps

3,4-Dimethoxybenzaldehyde (25 g, 0.15 mol), malonic acid (32.87 g, 0.31 mol) and piperidine (1 mL) were dissolved in pyridine (100 mL) under stirring. The reaction mixture was heated at 80° C. for 3 h, after which the temperature was further increased to 120° C. and maintained at this temperature for 3 h. The reaction mixture was cooled, diluted with water (70 mL) and pH of the solution was adjusted to 9 by addition of 10% aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate (3×150 mL). The pH of the aqueous layer was adjusted to 2 by addition of aqueous HCl (1:1) and the resulting solid was filtered and dried to afford the title compound.

Provenance & Evidence