Hydrochloric Acid → AY 22093

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Reaction Steps

A suspension of 15 g. of 15-hydroxy-9-oxoprostanoic acid, ethyl ester (Example 50) in 230 ml. of aqueous methanol (1:1) containing 6.45 g. 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, saturated with sodium chloride, and extracted several times wth diethyl ether. The combined ether extracts are washed twice with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and taken to dryness to give 13.1 g. (94%) of products as an oil. There is essentially no uv absorption; [αD25 0° (1.0% in CHCl3); λmaxKBr 2.80-3.70 (broad), 5.75, 5.87 μ; nmr 2H singlet δ6.65 (hydroxyl and carboxyl protons), 1H broad singlet 3.63 (carbinolic proton), and 3H distorted triplet 0.93 (terminal methyl); mass spectrum: m/e 340.

Provenance & Evidence