Acetone → HCID 5849647, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask equipped with magnetic stirrer and nitrogen inlet was charged with 2,4-dichlorobenzaldehyde (1.75 g, 10.0 mmol), acetone (44.1 ml, 0.60 mol) and water (20 ml). The mixture was cooled to 0° C. and a solution of sodium hydroxide (0.44 g, 11.0 mmol) in water (20 ml) was added drop wise during 1 hour to the vigorous stirred suspension. The reaction mixture was stirred for an additional 1.0 hour. The reaction mixture was concentrated in vacuo, poured onto 10% HCl (100 ml) and extracted with ethyl acetate (3×50 ml). Combined organic layers were dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (350 g) (eluent: n-hexane/ethyl acetate 1:1) to afford 1.9 g (88% of theory) of (E)-4-(2,4-dichloro-phenyl)-but-3-en-2-one in form of a pale yellow oil.

Provenance & Evidence