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

Participants

Reaction Steps

200 g of benzaldehyde, 176 g of cyanoacetic acid, 30 ml of acetic acid and 14.5 g of ammonium acetate were refluxed for 4 hours in 800 ml of ethyl alcohol with heating. After the reaction, the mixture was concentrated to 400 ml by removing the ethyl alcohol under a reduced pressure, followed by pouring into 1 liter of ice water to separate crystals. The resulting crystals were recrystallized from 250 ml of acetonitrile to obtain 265 g of 2-cyano-3-phenylacrylic acid having a melting point of 184° to 188° C. 150 g of the resulting compound and 176 g of thionyl chloride were dissolved in 100 ml of acetonitrile with heating for 1 hour. After the reaction, the acetonitrile and the thionyl chloride were distilled off under a reduced pressure, and the resulting solid was added to a solution containing 124 g of hydroxyethyl methacrylate, 75 g of pyridine and 1 liter of acetonitrile. The reaction was carried out for 2 hours while maintaining the reaction temperature below 40° C. After the reaction, the reacting solution was poured into ice water to separate crystals, and the resulting crystals were recrystallized from 1 liter of ethyl alcohol to obtain 205 g of the desired compound having a melting point of 68° to 70° C. The identification of the compound was carried out using IR spectrum, NMR spectrum and elemental analysis.

Provenance & Evidence