Preparation of alpha beta unsaturated ketone via the Aldol Condensation

J. Med. Chem, 1992, 35, 1853

Aldol condensation


Methyl ketone : 1 equivalent

Aldehdye : 1 eq

Sodium methoxide : 1.2 eq

Methanol : solvent

Alpha beta unsaturated ketone : variable yield expected.


To a solution of the methyl ketone and aldehyde (1 eq) in methanol was added sodium ethoxide (1.2eq).  The solution was heated to reflux for 2 h, cooled to room temperature, diluted with water, acidified with 2 N HCl, and extracted with EtOAc (3x).  The combined extracts were washed with water, brine, dried over Na2SO4, filtered, and concentrated to give the alpha beta unsaturated ketone.  The product above was recrystallized from 2-propanol to give a pale-yellow solid.  Yield = 25%.

NOTE: Low yield was probably due to low recovery in recrystallization.

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