Benzene → HCID 67265372, compound

Participants

Reaction Steps

To a suspension of lead tetraacetate (16.8 g) in benzene (80 ml) was added a solution of 2-methoxy-4-methylacetophenone (5.35 g) in methanol (8.25 ml), and then boron trifluoride/diethyl ether complex (16.5 ml) was added dropwise to the mixture with stirring under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was quenched with cold water, and extracted with benzene, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, water, and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give ethyl 2-methoxy-4-methylphenylacetate (3.22 g).

Provenance & Evidence