Sodium Cyanide → Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

Participants

Reaction Conditions

Reaction Steps

Into a flask were placed 755.7 g (2.5 moles) of the sodium salt of (hydroxy)(3-phenoxyphenyl)methanesulfonic acid, 237.6 g (1.25 moles) of sodium metabisulfite, and 2273 ml of water. The flask was cooled to 15° C. and a solution of 245.1 g (5.0 moles) of sodium cyanide in 302 ml of water was added dropwise. The reaction mixture was allowed to warm to room temperature, was stirred for 3 hours, then extracted three times with 800 ml of diethyl ether. The extract was washed once with 800 ml of a solution of 25% sodium metabisulfite and 1 N hydrochloric acid and twice with distilled water. After being dried over magnesium sulfate, the ether was evaporated, leaving a residue of 498.5 g of 94% (cyano)(3-phenoxyphenyl)methanol by gc analysis.

Provenance & Evidence