Acetic Anhydride → 4-Oxo-5-pentylcyclopent-2-en-1-yl acetate

Participants

Reaction Steps

Into a flask equipped with a stirrer and a thermometer, dl-3-hydroxy-2-n-pentyl-4-cyclopentenone (16.8 g), p-toluenesulfonic acid (0.1 g) and acetic anhydride (33.6 g) were charged, and the resultant mixture was stirred at 100° C. for 2 hours. After completion of the reaction, acetic anhydride was removed under reduced pressure, and the residue was extracted with toluene. The toluene layer was washed with 1% sodium bicarbonate solution and water. Toluene was removed from the toluene layer to give dl-3-acetoxy-2-n-pentyl-4-cyclopentenone (19.5 g). Yield, 93%. B.P., 105°-110° C./0.2-0.5 mmHg.

Provenance & Evidence