OXIMES. I. THE SYNTHESIS OF SOME SUBSTITUTED 2-OXIMINOACETOPHENONES,

The preparation of some p-omega-dimethylaminoalkyl- and pomega-dimethylaminoalkoxy-2oximinoacetophenones and their methiodides is described. No general method was found for synthesis of shortchain Co, C1, C2 p-omega-dimethylaminoalkyl-2oximinoacetophenones. The longer-chain compounds C3, C4 were prepared by a method which would appear to be general. Omega-Phenyl-1-haloalkanes undergo Friedel-Crafts acylation to yield p-omega-haloalkylacetophenones. These were converted to the dimethylamino compounds, which, subsequently, yielded 2oximinoacetophenones. No method of preparation of p-2-dimethylaminoethyl-2-oximinoacetophenone was found. Synthesis of p-omega-dimethylaminoalkoxy-2oximinoacetophenones was accomplished using mixed alpha,omega-dihaloalkanes and p-hydroxyacetophenone. The p-omega-haloalkoxy-acetophenones from these reactants were first converted to oximes and then to the dimethylamino compounds. Syntheses of p-omegadimethylamino-ethoxy, -propoxy, -butoxy, and -pentoxy2-oximinoacetophenones were achieved. That of pdimethylaminomethoxy-2-oximinoacetophenone was unsuccessful. Author