2,2-Dimethyl-3-heptanol → 2,2-Dimethyl-3-heptanone

HRID 39648노트

반응식

HRID 39648 반응식
[CH3:1][C:2]([CH3:10])([CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8])[CH3:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]([CH3:10])([C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8])[CH3:3]

참가 물질

4

반응물 2

HCID 1405432,2-Dimethyl-3-heptanolHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 1404722,2-Dimethyl-3-heptanone수율 89.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2,2-Dimethyl-heptan-3-ol (0.23 mol) was dissolved in 350 mL of CH2Cl2 in a 500 mL round bottom flask with a magnetic stirbar. The flask was partially cooled with ice. 76.6 g (0.355 mol) of pyridinium chlorochromate was added, while vigorously stirring. The reaction turned black and warmed up slightly. The reaction mixture was stirred at room temperature for 24 hours. The solution was decanted away from the black sludge, which was rinsed with hexane. The organic extracts were combined and chromatographed directly on silica gel. (Note: only silica has been found to trap and remove the reduced non-reacted chromium compounds). The product, 2,2-dimethyl-heptan-3-one, eluted with CH2Cl2/hexane and in a subsequent 10% ethyl acetate/hexane fraction to yield 29.19 g of product at 88% yield. 1H NMR (CDCl3, 500 MHz) δ (ppm): 2.48 (t, 2H), 1.54 (m, 2H), 1.28 (m, 2H), 1.13 (s, 9H), 0.90 (m, 3H).

후처리

  1. temperatureThe flask was partially cooled with ice
  2. temperaturewarmed up slightly
  3. stirringThe reaction mixture was stirred at room temperature for 24 hours
  4. customThe solution was decanted away from the black sludge, which
  5. washwas rinsed with hexane
  6. customchromatographed directly on silica gel
  7. custom(Note: only silica has been found to trap
  8. customremove the reduced non-reacted chromium compounds)
  9. washThe product, 2,2-dimethyl-heptan-3-one, eluted with CH2Cl2/hexane and in a subsequent 10% ethyl acetate/hexane fraction

출처 및 근거

ORD 기록
ord-007917ef16144e21af2f0b341cc5831d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524948B2

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