Water → HCID 10867554, compound

Participants

Reaction Conditions

Reaction Steps

To a vigorously stirred, ice-cold solution of chromic trioxide (5.4 g, 54 mmol) in 50 mL of 6N sulfuric acid was added dropwise over 3 hr, 1.76 g (8.9 mmol) of 20 in 50 mL of acetone5. The reaction was kept in an ice-bath for 30 min and then warmed to 23° C. before workup. Water (200 mL) was added and the reaction extracted with ether (4×75 mL). The ether extract was washed with brine (3×50 mL). Product isolation yielded crude 11-keto-3-dodecynoic acid (23) which was purified by crystallization from 10% ether in hexane (mp 49°-51° C.) to yield 1.28 g (68% yield).

Provenance & Evidence