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

HRID 133658

Reaction equation

HRID 133658 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 569245412-Azaniumylethylazanium;iron(2+);disulfate;tetrahydrateCatalystHCID 962WaterSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
50 °C

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-66f1bd7a3d27410ab1669a7fd5e30273
Source dataset
uspto-grants-2008_06
Patent number
US07390904B2

Linked notes

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