Acetic Acid → Ethyl 2-oxocyclopentanecarboxylate

Participants

Reaction Steps

15.0 g (0.652 mmol) of sodium was placed in 150 mL toluene, heated to reflux, shaken, and made into sodium sand. 81.6 g (0.400 mol) of diethyl adipate was added in drops to the mixture in an outside bath at 105-110° C., and the resultant solution changed into a yellow sticky product. After refluxing for 8 h, the solution was cooled by ice bath, and 400 mL of 10% acetic acid solution was added in drops. The mixture was suction filtered and washed with a small amount of toluene. The filtrate was separated into layers. The upper layer was washed with 7% sodium carbonate (260 mL×2) followed by saturated brine (200 mL×2), and dried overnight with anhydrous magnesium sulfate. The solution was filtered, concentrated and distilled under reduced pressure to collect the fractions of bp: 142-150° C./2660 Pa, yielding 53.3 g of colorless liquid with a yield of 85.6%.

Provenance & Evidence