Acetic Acid → 80540-68-7

Participants

Reaction Steps

Tolualdehyde (400 g), cyanoacetic acid (311 g), acetic acid (60 ml) and ammonium acetate (25.6 g) were refluxed for 4 hours by heating in ethyl alcohol (1.6 l). After the reaction, ethyl alcohol was concentrated to 600 ml under a reduced pressure, and it was poured in 1 liter of iced water to separate crystals. The separated crystals were filtered out by suction to obtain 2-cyano-3-(4-methylphenyl)acrylic acid which melted at 210°-215° C. in a yield of 560 g. This compound (320 g) and thionyl chloride (252 g) were dissolved in acetonitrile (200 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 (244.8 g), pyridine (149 g) and acetonitrile (2 liters). 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 iced water to separate crystals. The resulting crystals were recrystallized from ethyl alcohol (3 liters) to obtain 360 g of the desired product which melted at 74°-75° C.

Provenance & Evidence