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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence