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

Participants

Reaction Conditions

Reaction Steps

2,2′-Dipyridyl (0.056 g, 0.36 mmol) is stirred with 28 ml of acetonitrile. To the acetonitrile solution is added a solution of 0.098 g (0.36 mmol) of ferric chloride hexahydrate in 2 ml of water. This purple mixture is stirred for 10 minutes prior to adding 19 ml of cyclohexane and 5.00 g (18.1 mmol) of 1-oxyl-4-benzoyloxy-2,2,6,6-tetramethylpiperidine. A solution of 3.84 g (69.5 mmol) of 50% aqueous hydrogen peroxide is added to the reaction mixture dropwise over 2.25 hours while the temperature is brought to and maintained at 62° C. After the peroxide is added, the reaction mixture is heated at reflux for 1 hour. The reaction mixture is cooled, and peroxide is decomposed by the addition of aqueous sodium sulfite solution. Ethyl acetate is added, and the organic layer is washed with water. The organic layer is concentrated, and the concentrate is purified by flash chromatography with 20:1 heptane-ethyl acetate to afford 4.82 g (74% yield) of the title compound. GC assay is 100%.

Provenance & Evidence