Reaction of organomagnesium compounds with 2-bromo-1,3-cyclohexanedione

Summary Reaction of methylmagnesium iodide and of ethylmagnesium bromide with 2-bromo-1,3-cyclohexanedione (IV) gave 2-bromo-3-methyl- and 2-bromo-3-ethyl-2-cyclohexen-1-ones (X) and (XI)-, respectively. When these products were vacuum-distilled, they were converted into the m-substituted phenols (XII) and (XIII).Treatment of the bromocyclohexenones (X) and (XI) with dilute alkali gave the cyclic a-diketones (XVI) and (XVII).