Sodium Hydroxide → 7-[3,4-Dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoic acid

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Reaction Steps

Ethyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)-cyclopentyl]heptanoate (2.6 g.) [prepared as described in (p) above], ethanol (50 ml.) and 2N aqueous sodium hydroxide solution (50 ml.) were heated together at reflux for 18 hours. The ethanol was removed in vacuo, water (25 ml.) was added and the mixture was washed with diethyl ether. The aqueous phase {which was a solution of sodium 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate} was acidified to pH 1 by the dropwise addition of concentrated hydrochloric acid, extracted with diethyl ether, and the ethereal extract dried over magnesium sulphate and evaporated in vacuo to give 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoic acid (1.1 g.). Elemental analysis: found: C, 67.2; H, 10.3%. C20H38O5 requires C, 67.0; H, 10.7%.

Provenance & Evidence