Phenaglycodol
Phenaglycodol is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties. It is related pharmacologically to meprobamate, though it is not a carbamate.
Synthesis
p-Chloroacetophenone and potassium cyanide are reacted together via a Strecker reaction to give the corresponding cyanohydrin. The cyano group is then hydrated in acid to the corresponding amide, p-chloroatrolactamide. The amide group is then further hydrolyzed with a second equivalent of water in concentrated lye to give p-chloroatrolactic acid. Esterification then provides ethyl p-chloroatrolactate. Finally, nucleophilic addition with methylmagnesium iodide give phenaglycodol crystals.In a second method, a mixed pinacol coupling reaction between para-chloroacetophenone and acetone that was catalyzed by magnesium activated with a small amount of trimethylsilyl chloride gave a 40% yield of phenglycodol.