Methyl vinyl ketone → Sodium Hydroxide

Participants

Reaction Steps

The manufacture of the latter novel intermediates is exemplified by the consecutive synthetic steps involving first, reaction of 5-chloropent-1-yne with butyl lithium to form the corresponding lithium acetylide, reaction of that organometallic compound with boron trifluoride or boron trichloride to afford the tri-(5-chloropent-1-ynyl) boron derivative, which is reacted with methyl vinyl ketone to afford 9-chloro-5-nonyn-2-one, reaction of the latter substance with sodium cyanide in aqueous ethanol to yield 9-cyano-5-nonyn-2-one, saponification of that nitrile with aqueous sodium hydroxide in ethanol to produce 9-oxo-5-decynoic acid, followed by reduction of the olefinic double bond, thus affording the 9-oxo-5-decenoic acids. The cis-acid is conveniently produced by catalytic hydrogenation, e.g. with a palladium-on-barium sulfate catalyst in the presence of a catalyst poison such as quinoline, while the trans-acid is obtained by chemical reduction, e.g. with sodium and liquid ammonia.

Provenance & Evidence