Acetic Acid → 2-Cyano-3-phenylprop-2-enoic acid

Participants

Reaction Steps

Benzaldehyde (200 g), cyanoacetic acid (176 g), acetic acid (30 ml) and ammonium acetate (14.5 g) were refluxed for 4 hours by heating in ethyl alcohol (800 ml). After the reaction, ethyl alcohol was concentrated to 400 ml under a reduced pressure, and it was poured in 1 liter of iced water to separate crystals. The resulting crystals were recrystallized from 250 ml of acetonitrile to obtain 2-cyano-3-phenylacrylic acid which melted at 184°-188° C. in a yield of 265 g. This compound (150 g) and thionyl chloride (176 g) were dissolved in acetonitrile (100 ml) by heating for 1 hour. After the reaction, acetonitrile and thionyl chloride were distilled off under a reduced pressure, and the resulting solid was added to a solution composed of hydroxyethyl methacrylate (124 g), pyridine (75 g) and acetonitrile (1 liter). The reaction was carried out for 2 hours while keeping the reaction temperature at 40° C. or less. After the reaction, the reaction solution was poured in ice water to separate crystals. The resulting crystals were recrystallized from ethyl alcohol (1 l) to obtain 205 g of the desired product which melted at 68°-70° C.

Provenance & Evidence