Synthesis of Mixed Acyloins. V

Behaviors of Methylmagnesium Iodide towards Related Compounds of Mandelic Acid

Abstract

Mandelonitrile (A) or mandelimidic ester (e.g. ethyl mandelimidate) (B) reacts with methylmagnesium iodide to form phenylacetylcarbinol (I) and phenylmethylcarbinol (II). It has already been shown that the reaction of mandelamide (C) and methylmagnesium idodide afforded (I) but it was later clarified that (II) is also formed as a by-product in this synthesis. However, mandelic acid esters (e.g. ethyl mandelate) (D) reacts with methylmagnesium iodide and affords only 1-phenyl-2-methyl-1, 2-propanediol (III) and not (II).