Sodium Cyanide → HCID 20065474, compound

Participants

Reaction Conditions

Reaction Steps

Crude 1-chloro-1-(isobutylphenyl)ethane containing 47g of 1-chloro-1-(isobutylphenyl)ethane was added to a mixture of 17g of sodium cyanide in 126g of dimethyl sulfoxide (DMSO). The reaction mixture was heated to 80° C. with agitation for 10 hours, after which the DMSO and inorganic salts were removed by water washing to yield 1-cyano-1-(isobutylphenyl)ethane. The crude nitrile was reacted with excess 50% sodium hydroxide at 135.C for four hours to form the sodium salt of 2-(isobutylphenyl)propionic acid, which was then acidified and crystallized from hexane at -10.C. The para/ortho ratio of the resultant 2-(isobutylphenyl)propionic acid in hexane solution was approximately 200/1.

Provenance & Evidence