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

HRID 1910579Notes

Reaction equation

HRID 1910579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([O:11][CH3:12])=[C:6]([CH:8]([OH:10])[CH3:9])[CH:7]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 140929151-(5-Chloro-2,3-dimethoxyphenyl)ethanolHCID 131709961Jones' reagent

Product 1

HCID 140929161-(5-Chloro-2,3-dimethoxyphenyl)ethanoneYield 63.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-3c97ea92aa9a468e8e8dee21b084af99
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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