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

HRID 733177

반응식

HRID 733177 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6715ea02b06f4d54891d740e2a2ec68f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589095B2

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