Synthesis of 2,2-dimethyl-4-hexanone via Grignard additions to tert.-butylacetyl-chloride and tert.-butylacetonitrile

Jean Clipsham


The compound 2,2-dimethyl-4-hexanone was synthesized for use in an experiment, to furnish further auxiliary evidence for the proposed mechanism of oxidation of tetronic acids. This mechanism was derived from work done by Dr. Reid and his associates. Their preliminary studies dealt with the structural criteria of the tetronic acid necessary for the formation of ?-diketones 1.) On oxidation of a tetronic acid where the 3-carbon atom is monosubstituted, ?-diketones are formed regardless of the substitution on the 5-carbou atom. This process consists of a decarboxylation with oxidation of the 3-carbon atom and reduction of the 5-carbon atom. 2.) If the 3-carbon atom is unsubstituted, the 5-carbon atom must have only one substitution in order to produce the ?-diketone. Oxidation takes place at the 5-carbon atom and reduction at the 3-carhon.