Τίτλος:
A new protocol for a regioselective aldol condensation as an alternative convenient synthesis of β-ketols and α,β-unsaturated ketones
Γλώσσες Τεκμηρίου:
Αγγλικά
Περίληψη:
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, giving the β-ketol in high yield (75-90%). Acidification of the reaction mixture at pH 1 and heating at 70 °C under vigorous stirring for 6 h, leads directly to the corresponding α,β-unsaturated ketone in good yield (65-75%).
Συγγραφείς:
Kourouli, T.
Kefalas, P.
Ragoussis, N.
Ragoussis, V.
Περιοδικό:
The Journal of Organic Chemistry
Λέξεις-κλειδιά:
Acidification, Aldehydes; Condensation; pH effects; Potassium compounds; Salts; Saponification; Synthesis (chemical), Ketones, alkene; carboxylic acid derivative; ketol; ketone derivative; oxoacid; potassium hydroxide; potassium salt, acidification; article; chemical reaction; decarboxylation; molecular interaction; pH; polymerization; reaction analysis; synthesis
