4-Chlorobenzoic Acid → Ethyl 3-(4-chlorophenyl)-3-oxopropanoate

Participants

Reaction Steps

To a suspension of potassium ethyl malonate (8.2 g) in ethyl acetate (100 mL), triethylamine (17 mL) and magnesium chloride (5.5 g) were added under ice cooling. The temperature of the resultant mixture was returned gradually to room temperature, and the mixture was stirred for 18 hours. In addition, a suspension of 4-chlorobenzoic acid (5.0 g), thionyl chloride (12 mL), N,N-dimethylformamide (1 drop), and toluene (100 mL) was heated under reflux for 1 hour, and the reaction mixture was concentrated. The residue was dissolved in ethyl acetate, and the solution was added dropwise to the above mixture under ice cooling. The temperature of the mixture was gradually returned to room temperature, and the mixture was stirred for 18 hours. 10% Aqueous citric acid was added to the reaction mixture, and the mixture was stirred for 30 minutes, and the organic layer was partitioned. The resultant organic layer was washed with saturated brine, followed by drying over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure. The residue was separated and purified by silica gel column chromatography (chloroform), to thereby give the title compound (6.4 g).

Provenance & Evidence