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A piperidone-4 with a suitable alkyl substituent in the 3-position could conceivably function as starting material for a synthesis of homomeroquinene (2);* no compound of this type has been reported in the literature (3). This paper describes the preparation of 1,3-dimethylpiperidone-4 (IV) by the steps outlined below; this type of synthesis has been employed extensively by McElvain and co-workers (4).

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Ziegler Bromination of Methylenecyclobutane 2517 No secondary alcohol was detected; the larger part of the liquid began to decompose and carbonize at a bath temperature of 180°and pressure of 4 mm.An average of results from two runs gave amorphous solid, 12.5 g.; dibenzyl, 6.3 g.; tarry, carbonaceous residue, 14.5 g.Table I provides essential data. Yields in each case are averages from two runs. Summary 1. The reaction of a, /3-dichloropropionaldehyde with phenylmagnesium bromide, «-hexyl-magnesium bromide, cyclohexylmagnesium bromide, /3-phenylethylmagnesium bromide and benzylmagnesium chloride has been studied.2. The new secondary alcohols 2,3-dichloro-lphenylpropanol-1, l,2-dichlorononanol-3, 2,3-dichloro-1 -cyclohexylpropanol-1 and l,2-dichloro-5phenylpentanol-3 have been prepared via the Grignard reaction. Akron, Ohio