Acetone → 6-Phenylhexa-3,5-dien-2-one

Participants

Reaction Steps

In a 250 ml single neck flask was charged 13.2 g (100 mmoles,1.0 eq) of cinnamaldehyde dissolved in 30 ml of acetone. To this was added 5 g of 10% aqueous sodium hydroxide solution (12.5 mmoles, 0.125 eq), dropwise and during the course of addition, temperature was kept no higher than 25° C., while the mixture was agitated continuously for 30 minutes. To the mixture was added 50 ml of water, followed by 100 ml of ethyl acetate, the phases were separated and the organic phase was washed with water three times and then dried, and concentrated to obtain 15.7 g of 4-(2-phenylethenyl)-3-buten-2-one as a faintly yellow oil in 91% yield.

Provenance & Evidence