Acetic Acid → 80540-68-7

Participants

Reaction Steps

400 g of tolualdehyde, 311 g of cyanoacetic acid, 60 ml of acetic acid and 25.6 g of ammonium acetate were refluxed in 1.6 liters of ethyl alcohol for 4 hours with heating. After the reaction, the mixture was concentrated to 600 ml by removing the ethyl alcohol under a reduced pressure, followed by pouring into 1 liter of ice water to separate crystals. The separated crystals were collected by suction filtration and recrystallized from 2 liters of ethyl alcohol to obtain 560 g of 2-cyano-3-(4-methylphenyl)acrylic acid having a melting point of 210 to 215° C. 320 g of the resulting compound and 252 g of thionyl chloride were dissolved in 200 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 244.8 g of hydroxyethyl methacrylate, 149 g of pyridine and 2 liters 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 3 liters of ethyl alcohol to obtain 360 g of the desired compound having a melting point of 74° to 75° C. The identification of the compound was carried out using IR spectrum, NMR spectrum and elemental analysis.

Provenance & Evidence