1-(5-Chloro-2,3-dimethoxyphenyl)ethanol → 1-(5-Chloro-2,3-dimethoxyphenyl)ethanone

Participants

Reaction Steps

To a solution of 1-(5-chloro-2,3-dimethoxy-phenyl)-ethanol (5.67 g, 26.8 mmol) in acetone (200 mL) at room temperature was added a previously prepared solution of Jones Reagent (H2O—H2SO4—CrO3, 100 mL/22 mL/20 g) (100 mL, dropwise). The reaction was stirred for 3 h, and then concentrated. The mixture was dissolved in ethyl acetate (200 mL) and washed with 3.0 N aqueous NaOH and brine. The organic phase was dried over Na2SO4, filtered over silica gel, and concentrated to the crude compound which was purified by silica gel column (20% ethyl acetate in hexanes) to afford 1-(5-chloro-2,3-dimethoxy-phenyl)-ethanone (3.65 g, 63%): 1H NMR (400 MHz, CDCl3): δ 7.20 (d, 1 H), 7.00 (d, 1 H), 3.89 (s, 6 H), 2.62 (d, 3 H).

Provenance & Evidence