Reaction of Grignard reagents with β-dicarbonyl compounds. II. Synthesis of β-hydroxyketones from 2,4-pentanedione

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<jats:p> Several new β-hydroxyketones having the formula CH<jats:sub>3</jats:sub>R′C(OH)CH<jats:sub>2</jats:sub>COCH<jats:sub>3</jats:sub> have been prepared by the action of Grignard reagents on 2,4-pentanedione. With benzyl-, o-xylyl-, p-xylyl-, 3,4-dimethylbenzyl-, 2,5-dimethylbenzyl-, 3,5-dimethylbenzyl-, and α-naphthylmethyl-magnesium chlorides, 60 to 75% yields of the β-hydroxyketones were obtained. Phenyl-, p-tolyl-, and p-trifluoromethylphenyl-magnesium bromide and 2,4-dimethylbenzylmagnesium chloride gave lower yields, whereas with α-naphthylmagnesium bromide no β-hydroxyketone was formed. The β-hydroxyketones were separated from non-ketonic by-products by means of Girard's reagent T or P. Solid derivatives of the β-hydroxyketones could not be prepared. </jats:p>

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