Benzaldehyde → HCID 70102567, compound

Participants

Reaction Steps

To a solution of potassium tert-butoxide (16.8 g) in tert-butyl alcohol (150 ml) is added dropwise with stirring a solution of benzaldehyde (15.9 g) and dimethyl succinate (26.3 g) in tert-butyl alcohol (20 ml) at room temperature, and the mixture is stirred for 30 minutes. The reaction mixture is poured into ice-water (200 ml), and the mixture is extracted with isopropyl ether. The pH value of the aqueous layer is adjusted to pH 2-3, and extracted with ethyl acetate. The extract is washed, dried, and concentrated under reduced pressure. The residue is dissolved in a mixture of toluene (50 ml) and ethylene glycol monomethyl ether (50 ml), and thereto is added dropwise thionyl chloride (16.4 ml) at 0° C. The mixture is allowed to stand at room temperature overnight, and the mixture is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; hexane: ethyl acetate=4:1) to give (E)-3-methoxycarbonyl-4-phenyl-3-butenoic acid 2-methoxyethyl ester (26.9 g).

Provenance & Evidence