Hydrochloric Acid → alpha-Methyl-4-nitrocinnamic acid

Participants

Reaction Steps

630 ml of pyridine was added to 76 g of 4-nitrobenzaldehyde (m.p. 105°-106.5° C.), 118 g of methylmalonic acid (prepared by hydrolysis of diethyl methylmalonate) and 85 g of piperidine. The mixture was heated with stirring over a steam bath for 24 hours. After being allowed to cool, the reaction mixture was then added to a mixture of 1,250 ml of concentrated hydrochloric acid and 2.5 kg of ice. The resulting oil content was then extracted with diethyl ether. The oil content was further extracted with a 5% aqueous solution of sodium hydroxide. The aqueous solution was then slightly acidified. The resulting crystal composition was then filtered off and dried. (Yield: 86 g (83%))

Provenance & Evidence