Methyl vinyl ketone → HCID 54188104, compound

Participants

Reaction Conditions

Reaction Steps

Butenone (7.23 cc) is added to a solution of bis-(3-tolyl)acetaldehyde (20.4 g) in ethyl ether (110 cc) and then, after cooling to 0° C., a solution of potassium hydroxide (2 g) in ethanol (12.7 cc) is added dropwise. The reaction mixture is stirred for 2 hours at 0° C. and then for 16 hours at 25° C. and diluted with ethyl acetate (200 cc) and water (200 cc). The aqueous phase is washed with ethyl acetate (2×250 cc). The combined organic phases are washed with water (2×250 cc) and then with saturated sodium chloride solution (250 cc), dried over magnesium sulphate and concentrated under reduced pressure (2.7 kPa). The residue is chromatographed on silica gel (particle size 0.04-0.063 mm, column 5.4 cm in diameter and 40 cm high), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (85/15 by volume). 4,4 -bis-(3-Tolyl)-cyclohexenone (16.7 g) is obtained in the form of yellow oil.

Provenance & Evidence