Sodium Hydroxide → HCID 15839729, compound

Participants

Reaction Steps

A solution of ethyl 7-[3-(4-acetyl-2-ethyl-5-hydroxyphenoxy)propoxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate in dioxane (3.5 M solution) was treated with 2N sodium hydroxide (3.0 eqv) and stirred at room temperature. After stirring for 4 hours, the dioxane was removed from the reaction, and the remaining solution was diluted with water and acidified with 5N hydrochloric acid. The resulting milky solution was extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and filtered. Solvent removal gave a white solid. The solid was purified by flash chromatography on silica gel eluting with 50% ethyl acetate/hexane, and the resulting solid was crystallized from ethyl acetate and hexane. The desired acid was obtained in 47% yield.

Provenance & Evidence