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

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Abstract
The preparation of some p-(ω′-dimethylaminoalkyl)- and p-(ω′-dimethylaminoalkoxy)-2-oximinoacetophenones and their methiodides is described.No general method was found for synthesis of short-chain (C0, C1, C2) p-(ω′-dimethylaminoalkyl)-2-oximinoacetophenones. The longer-chain compounds (C3, C4) were prepared by a method which would appear to be general. ω-Phenyl-1-haloalkanes undergo Friedel–Crafts acylation to yield p-(ω′-haloalkyl)-acetophenones. These were converted to the dimethylamino compounds, which, subsequently, yielded 2-oximinoacetophenones. No method of preparation of p-(2′-dimethylaminoethyl)-2-oximinoacetophenone was found.Synthesis of p-(ω′-dimethylaminoalkoxy)-2-oximinoacetophenones was accomplished using mixed α,ω-dihaloalkanes and p-hydroxyacetophenone. The p-(ω′-haloalkoxy)-acetophenones from these reactants were first converted to oximes and then to the dimethylamino compounds. Syntheses of p-(ω′-dimethylamino-ethoxy, -propoxy, -butoxy, and -pentoxy)-2-oximinoacetophenones were achieved. That of p-(dimethylaminomethoxy)-2-oximinoacetophenone was unsuccessful.

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