Azobisisobutyronitrile → Ethyl 2-(3-formylphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

N-bromosuccinimide (1.78 g) and 2,2′-azobis(2-methylpropionitrile) (16 mg) were added to a solution of ethyl-3-methylphenylacetate (1.76 mL) in chloroform (18 mL) and heated to reflux for 3 hours. On cooling the mixture was diluted with chloroform (40 mL), washed sequentially with saturated aqueous sodium bicarbonate solution (2×50 mL), brine (50 mL), dried (sodium sulfate) and concentrated. The residue was dissolved in nitrogen degassed dimethylsulfoxide (50 mL) and sodium bicarbonate (13.5 g) added. The mixture was heated at 100° C., under nitrogen for 30 min. The reaction was cooled in an ice-bath and poured into brine (300 mL). The aqueous phase was extracted with diethyl ether (3×300 mL). The combined organics were dried (sodium sulfate) and concentrated. Purification on silica, eluting with 10% diethyl ether in iso-hexane, to afford the subtitle compound as a yellow oil (1.23 g).

Provenance & Evidence