Barium bromate → 1-(3-tert-Butylphenyl)ethan-1-one

Participants

Reaction Steps

To a stirring solution of 1-tert-butyl-3-ethylbenzene (11.15) in acetonitrile (350 ml) and water (150 ml) at room temperature was added cerium (III) sulfate (6.05 g) and barium bromate (13.5 g). The resulting suspension was heated at reflux for 16 hrs. After cooling to room temperature, the reaction mixture was filtered. Saturated aqueous sodium thiosulphate solution was added to the filtrate, and the product was extracted into DCM (3×100 ml). Combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo to give 1-(3-tert-butyl-phenyl)-ethanone as a yellow oil crude product (13.5 g). 1H NMR (CDCl3): δ 8.00 (s, 1H), 7.75 (d, 1H), 7.61 (d, 1H), 7.39 (t, 1H), 2.61 (s, 3H), 1.36 (s, 9H).

Provenance & Evidence