Hydrogen Peroxide → 1-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 133658

반응식

HRID 133658 반응식
CS(O)(=O)=O.[OH:6][N:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH:10]([OH:15])[CH2:9][C:8]1([CH3:17])[CH3:16].[C:18](#N)[CH3:19].OO>O.O.O.O.O.S([O-])([O-])(=O)=O.C([NH3+])C[NH3+].[Fe+2].S([O-])([O-])(=O)=O.C1CCCCC1>[CH:19]1([O:6][N:7]2[C:12]([CH3:13])([CH3:14])[CH2:11][CH:10]([OH:15])[CH2:9][C:8]2([CH3:17])[CH3:16])[CH2:18][CH2:10][CH2:9][CH2:8][CH2:16]1

참가 물질

8

반응물 4

HCID 784Hydrogen PeroxideHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 6342AcetonitrileHCID 6395Methanesulfonic Acid

생성물 1

HCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol수율 53%

시약·촉매·용매 3

HCID 569245412-Azaniumylethylazanium;iron(2+);disulfate;tetrahydrate촉매HCID 962Water용매HCID 8078Cyclohexane용매

반응 조건

온도
50 °C

실험 절차

A solution of 0.404 g (1.1 mmol) of iron(II) ethylenediammonium sulfate tetrahydrate and 0.237 g (2.5 mmol) of methanesulfonic acid in 2 ml of water is added to a mixture of 5.00 g (29.0 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 38 ml of acetonitrile, and 24 ml of cyclohexane. The reaction mixture is heated to 50° C. A solution of 8.0 g (118 mmol) of 50% aqueous hydrogen peroxide is added to the reaction mixture dropwise over 4 hours while the temperature is brought to and maintained at reflux. After the peroxide is added, the reaction mixture is allowed to cool slowly to room temperature. The reaction mixture is stirred overnight at ambient temperature. The lower layer is discarded, and the organic layer is concentrated and purified by flash chromatography to afford 3.9 g (53% yield) of the title compound, a yellow solid. GC assay is greater than 99%.

후처리

  1. temperaturemaintained
  2. temperatureat reflux
  3. temperatureto cool slowly to room temperature
  4. concentrationthe organic layer is concentrated
  5. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-66f1bd7a3d27410ab1669a7fd5e30273
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390904B2

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