Hydrochloric Acid → HCID 13987403, compound

Participants

Reaction Steps

A magnetically stirred mixture comprising 2.10 g (0.01 mole) of twice distilled 2-hydroxy-5,5,-dimethyl-3-hexynoate, n-butyl 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 four 35 ml portions of water and dried over MgSO4. Filtration and concentration at the stripper afforded 1.20 g (75% yield) of 2-hydroxy-5,5-dimethyl- 3-hexynoic acid, a light yellow, viscous oil. Pumping down at 25° C./0.20 mm for one hour produced no observable reduction in product weight.

Provenance & Evidence