tert-Butyl hydroperoxide → 4-Benzoyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine

HRID 1493525

반응식

HRID 1493525 반응식
[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24]O)([CH3:23])(C)C>[Mo](=O)(=O)=O.CCCCCCCC>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([O:24][CH2:20][CH2:23][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])[C:12]([CH3:19])([CH3:18])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 6410tert-Butyl hydroperoxideHCID 5799672,2,6,6-Tetramethyl-4-piperidyl benzoate

생성물 1

HCID 151699944-Benzoyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine

시약·촉매·용매 2

HCID 14802Molybdenum trioxide촉매HCID 356Octane용매

반응 조건

온도
120 °C

실험 절차

A mixture of 55.3 grams (0.2 mol) of 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 2.8 grams of molybdenum trioxide and 250 ml of n-octane is heated to 120° C. A solution of 90.2 grams (0.7 mol) of 70% aqueous tert-butyl hydroperoxide is added dropwise to the hot reaction mixture. Water is removed by azeotropic distillation and collected in a Dean-Stark trap. The reaction mixture is heated at reflux till the red color of the intermediate N-oxyl compound disappears. Solids are removed by filtration, and the filtrate is concentrated under vacuum to give an oil. Purification of the oil by flash chromatography on silica gel (100:3 heptane: ethyl acetate) affords 4-benzoyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine as a mixture of octyloxy isomers. Further elution of the chromatographic column with 50:3 heptane:ethyl acetate affords the title compound as a mixture of octanediyl isomers.

후처리

  1. customWater is removed by azeotropic distillation
  2. customcollected in a Dean-Stark trap
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux till the red color of the intermediate N-oxyl compound
  5. customSolids are removed by filtration
  6. concentrationthe filtrate is concentrated under vacuum
  7. customto give an oil
  8. customPurification of the oil by flash chromatography on silica gel (100:3 heptane: ethyl acetate)

출처 및 근거

ORD 기록
ord-3fb9a37cc3b047c498cccbbc2b2d7b7b
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05021577

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