Acrylic Acid → 2-Propenoic acid, 2,5-dioxo-1-pyrrolidinyl ester

Participants

Reaction Steps

To a mixture of 400 ml of chloroform, 115 g of N-hydroxysuccinimide and 72 g of acrylic acid in a reaction vessel, 206 g of N,N-dicyclohexylcarbodiimide dissolved in 100 ml of chloroform was added dropwise over a period of 2 hours under cooling with ice water. Following a 2-hour stirring at room temperature, the precipitate was filtered off and the filtrate concentrated at low temperature for crystallization. The resulting crystals were filled to give 116 g of N-acryloyloxysuccinimide (mp=61°-62° C., yield=68%). The active ester content was determined by the method of Ronald L. Schnaar and Yuan Chuan Lee described in Biochemistry, p. 1535 (1975) as 5.2×10-3 eq./g.

Provenance & Evidence