Hydrochloric Acid → HCID 14421664, compound

Participants

Reaction Steps

A solution of 10 g of 5-[3-hydroxy-4-(2 -hydroxybenzoyl)-2-propylphenoxy]pentanenitrile and 12.9 g of potassium hydroxide in approximately 250 ml of 10% methanol/water was heated at reflux for 5 days. The solution was cooled to room temperature, acidified with hydrochloric acid. The crude product which precipitated was recovered by filtration and purified by high pressure liquid chromatography over silica gel eluting with a 30-40% ethyl acetate in hexane gradient containing 0.5% acetic acid. The appropriate fractions were combined, evaporated, and recrystallized from diethyl ether/hexane to provide 8.0 g of the desired title carboxylic acid, m.p. 88.5°-91.5° C.

Provenance & Evidence