Reaction of Grignard reagents with β-dicarbonyl compounds. II. Synthesis of β-hydroxyketones from 2,4-pentanedione
- 1 August 1967
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 45 (15) , 1761-1765
- https://doi.org/10.1139/v67-284
Abstract
Several new β-hydroxyketones having the formula CH3R′C(OH)CH2COCH3 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.Keywords
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