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

Participants

Reaction Conditions

Reaction Steps

A solution of 0.100 g (0.360 mmol) of ferrous sulfate heptahydrate and 0.112 g (1.82 mmol) of boric acid in 4 ml of water is added to a mixture of 5.00 g (18.1 mmol) of 1-oxyl-4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 27 ml of acetonitrile, and 19 ml of cyclohexane. The mixture is heated to 52° C. A solution of 4.98 g (73 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 2.75 hours to the reaction mixture while the temperature is brought to and maintained at reflux (63° C.). A solution of 0.051 g of ferrous sulfate heptahydrate and 0.042 g of boric acid in 2 ml of water is added to the reaction mixture 1.25 hours after the peroxide addition is started. After the peroxide is added, the reaction mixture is heated at reflux for 30 minutes, then allowed to cool slowly. Work-up and purification according to the procedure of Example 5 afford 4.42 g (68% yield) of the title compound, a colorless syrup, GC assay 99.3%.

Provenance & Evidence