Potassium Hydroxide → 9-Ethylenedioxy-15-hydroxy-15-methyl-prostanoic acid

Participants

Reaction Steps

A solution of 1.33 g. of ethyl 9-ethylenedioxy-15-hydroxy-15-methyl prostanoate (Example 57) in 20 ml. of methanol-water (1:1) containing 500 mg. of potassium hydroxide is stirred at room temperature for 18 hours. The solution is neutralized with 30% aqueous sodium phosphate monobasic and extracted with ether. The ether extract is washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 1.23 g. (99%) of viscous oil; λ max. 2.94-4.00 (broad) (hydroxyl and carboxyl groups) and 5.85 μ (acid carbonyl group).

Provenance & Evidence