4-Hydroxybenzaldehyde → P-Coumaric Acid

Participants

Reaction Conditions

Reaction Steps

Malonic acid, 813 g, was added to p-hydroxy benzaldehyde, 472 g, in pyridine, 957 ml. The mixture was heated to 65° C. and aniline, 28 ml, was added. The reaction was stirred at 65° C. for 7.5 hours and then cooled to room temperature. HCl, 2.75 L, 2N HCl, was then added dropwise while the reaction stirred A creamy precipitate formed. The reaction was stirred for an additional 10 minutes. The precipitate was collected by filtration and dried under reduced pressure. The solid was identified as coumaric acid by IR spectroscopy. The yield was ≥80%.

Provenance & Evidence