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

HRID 733177

Reaction equation

HRID 733177 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S([O-])([O-])(=O)=[O:14].[Ce+3].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Ce+3].Br([O-])(=O)=O.[Ba+2].Br([O-])(=O)=O>C(#N)C.O>[C:1]([C:5]1[CH:6]=[C:7]([C:11](=[O:14])[CH3:12])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 61706Barium bromateHCID 1397531-t-Butyl-3-ethylbenzeneHCID 159674Cerous sulfate

Product 1

HCID 136579781-(3-tert-Butylphenyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 16 hrs
  3. filtrationthe reaction mixture was filtered
  4. additionSaturated aqueous sodium thiosulphate solution was added to the filtrate
  5. extractionthe product was extracted into DCM (3×100 ml)
  6. washCombined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6715ea02b06f4d54891d740e2a2ec68f
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Linked notes

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