Esters of Dimethylethylacetic Acid.

Rearrangement in the Reaction Between Thionyl Chloride and 3-Methyl-2-Butanol

“…The infrared absorption spectruill of this product showed all the absorption peaks as l;no~~rn t-arnyl chloride together with an extra, weal; and broad band in the 1726 to 1750 cm-I region. These results appear to indicate that the reactioil product may be t-amyl chloride contaminatcd with a small amount of un1;nown inzpurity.T o coilfirin the identity of the reaction product as chiefly t-amyl chloride, it was converted to the Grigilard reagent followed by reaction with carboil dioxide to give dimethylethylacetic acid (7,8) with an over-all yield of 35%. The low yield was to be expected since it is difficult to prepare Grignard reagents froill t-alkyl halides.…”

“…T o coilfirin the identity of the reaction product as chiefly t-amyl chloride, it was converted to the Grigilard reagent followed by reaction with carboil dioxide to give dimethylethylacetic acid (7,8) with an over-all yield of 35%. The low yield was to be expected since it is difficult to prepare Grignard reagents froill t-alkyl halides.…”