Hydrogen Peroxide → 1-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

HRID 133656Notes

Reaction equation

HRID 133656 reaction equation
F[C:2](F)(F)[C:3](O)=O.[OH:8][N:9]1[C:14]([CH3:16])([CH3:15])[CH2:13][CH:12]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][C:10]1([CH3:27])[CH3:26].OO.S([O-])([O-])=O.[Na+].[Na+]>O.F[P-](F)(F)(F)(F)F.C1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].C1CCCCC1.C(#N)C>[CH:3]1([O:8][N:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH:12]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:11][C:10]2([CH3:27])[CH3:26])[CH2:2][CH2:12][CH2:11][CH2:10][CH2:26]1

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 24437Sodium SulfiteHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 233720981-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidineYield 514.6%

Reagents, catalysts & solvents 4

HCID 131726945Cyclopenta-1,3-diene;cyclopenta-1,3-diene;iron(2+);hexafluorophosphateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 0.237 g (0.72 mmol) of ferrocenium hexafluorophosphate in 0.269 g (2.4 mmol) of trifluoroacetic acid and 3 ml of water is added to a mixture of 5.01 g (18.1 mmol) of 1-oxyl-4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 25 ml of acetonitrile, and 16 ml of cyclohexane. The reaction mixture is heated to 50° C. A solution of 5.0 g (73 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 2 hours to the reaction mixture while the temperature is brought to and maintained at 62° C. After the peroxide is added, the reaction mixture is heated at 62° C. for 30 minutes. The reaction mixture is cooled slowly to room temperature and stirred overnight. Peroxide is decomposed by the addition of aqueous sodium sulfite solution. Work-up with ethyl acetate and purification by flash chromatography afford 4.44 g (68% yield) of the title compound.

Workup

  1. temperaturemaintained at 62° C
  2. temperaturethe reaction mixture is heated at 62° C. for 30 minutes
  3. temperatureThe reaction mixture is cooled slowly to room temperature
  4. customWork-up with ethyl acetate and purification by flash chromatography

Sources & evidence

ORD record
ord-4eb5542aa43f4cec92dd777805d4daaa
Source dataset
uspto-grants-2008_06
Patent number
US07390904B2

Reaction notes

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