A new protocol for a regioselective aldol condensation as an alternative convenient synthesis of β-ketols and α, β-unsaturated ketones

…, P Kefalas, N Ragoussis, V Ragoussis

Index: Kourouli, Therapia; Kefalas, Panagiotis; Ragoussis, Nikitas; Ragoussis, Valentine Journal of Organic Chemistry, 2002 , vol. 67, # 13 p. 4615 - 4618

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Citation Number: 52

Abstract

A general and convenient synthesis of β-ketols and α, β-alkenones has been achieved by a Knoevenagel condensation of a β-ketoacid with an aldehyde in aqueous medium. Saponification of a β-ketoester by an aqueous KOH 10% solution gives the potassium salt of the β-ketoacid, which is condensed in situ with an aldehyde at pH 7.8-8.0, at 60° C for 5-6 h. The intermediate β-ketocarboxylate is smoothly decarboxylated in the reaction medium, ...