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

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, 1H), 7.00 (d, 1H), 3.89 (s, 6H), 2.62 (d, 3H).

1. concentrationconcentrated
2. dissolutionThe mixture was dissolved in ethyl acetate (200 mL)
3. washwashed with 3.0 N aqueous NaOH and brine
4. dry with materialThe organic phase was dried over Na2SO4
5. filtrationfiltered over silica gel
6. concentrationconcentrated to the crude compound which
7. customwas purified by silica gel column (20% ethyl acetate in hexanes)

ORD-Eintrag

ord-860077de8c044c83ab6c854850b0fb7b

Quelldatensatz

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07968538B2