Acrylic Acid → 2-Oxocyclohexanepropanoic acid

Participants

Reaction Steps

29.4 Grams (0.300 mol; 31.1 mL) cyclohexanone, 14.4 grams (0.200 mol; 13.7 mL) of acrylic acid, 1.6 mL (9.6×10-3 mol) of 1-pyrrolidino-1-cyclohexene and 0.09 grams (5×10-3 mol) of water were added to a 250 mL round bottomed flask equipped with a reflux condenser, thermometer, and magnetic stirrer. The mixture was stirred and heated under reflux for four hours. The mixture was then cooled to room temperature resulting in a slushy mixture. Next, the reaction product was subjected to fractional distillation using a 1×20 cm Vigreux column and 0.3 mm Hg vacuum. The fraction taken at 145-151° C. yielded 20.4 g of 91 percent 3-(2-oxocyclohexyl)-propanoic acid (54 percent yield). This fraction was recrystallized in 40 mL CHCl3 /200 mL petroleum ether to give 15.4 grams of 3-(2-oxocyclohexyl)propanoic acid at 99 percent purity.

Provenance & Evidence