Hydrochloric Acid → HCID 13987404, compound

Participants

Reaction Steps

A magnetically stirred mixture of 2.20 g (0.01 mole) of twice distilled 2-hydroxy-2-methyl-4-phenylbutynoate, ethyl ester 1.40 g (0.01 mole) of potassium carbonate and 3 ml of methanol in 20 ml of water was heated under a dry nitrogen atmosphere at 75°-80° C. for 1.5 hours, during which time the substrate dissolved to afford a faint yellow solution. After cooling, 20 ml of water was added and the solution was exhaustively extracted with ether. The aqueous phase was then treated with 1.5 g of Darco® activated carbon, filtered with suction through a Celite® pad and acidified in an ice bath with 2.0 ml (0.02 mole) of concentrated hydrochloric acid. The resulting oil was extracted with three 25 ml portions of ether and the combined extracts were washed with three 35 ml portions of water and dried over MgSO4. Filtration and concentration at the stripper provided an almost colorless oil which solidified on cooling. Recrystallization from hexane containing a trace of ether afforded 1.60 g (89% yield) of 2-hydroxy-2-methyl-4-phenylbutynoic acid as colorless plates, m.pt. 104.5°-106.0° C.

Provenance & Evidence