Hydrochloric Acid → 9-Oxoprostanoic acid

Participants

Reaction Steps

A suspension of 300 mg. of ethyl 9-oxoprostanoate in 20 ml. of aqueous methanol (1:1) containing 300 mg. of potassium hydroxide is stirred at 50° C. for 1 hour and then at room temperature for 18 hours. The resulting solution is acidified with 1N hydrochloric acid, concentrated and extracted several times with diethyl ether. The combined ether extracts are washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 256 mg. (94%) of product as an oil;λmax 5.75, 5.85 μ; nmr 1H broad singlet δ 9.89 (carboxyl proton, exchangeable).

Provenance & Evidence