Acrylic anhydride → Acrylic Acid
Reaction equation
[C:1]([O:5][C:6](=[O:9])[CH:7]=[CH2:8])(=[O:4])[CH:2]=[CH2:3].NCCC1C=CN=CC=1>>[C:1]([O:5][C:6](=[O:9])[CH:7]=[CH2:8])(=[O:4])[CH:2]=[CH2:3].[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[C:1]([O:5][C:6](=[O:9])[CH3:7])(=[O:4])[CH3:2]Participants
5
Procedure
This substituted acrylamide was synthesized from acrylic anhydride and 4-(2-aminoethyl)pyridine. Acrylic anhydride was obtained from acrylic acid and acetic anhydride. Synthesis of PEAM was initiated by the slow addition of 0.36 mole (45.0 g) of acrylic anhydride in 50 ml of ethyl ether containing 50 mg of BHT to 0.35 mole (42.76 g) of 4-(2-aminoethyl)pyridine in 150 ml of ethyl ether containing 150 mg of BHT at -55° C., with the formation of a precipitate. The rate of addition was kept sufficiently slow to ensure that the temperature did not exceed -30° C. during the reaction. After removal of the ether by room temperature evaporation, the precipitate was dissolved in 200 ml of methanol and subsequently vacuum distilled. The substituted acrylamide (15% yield) was collected at 170° C., 100 mtorr.