tert-Butyl hydroperoxide → HCID 70374144, compound

Participants

Reaction Steps

A mixture of 25.0 g (0.052 mol) of bis(2,2,6,6-tetramethylpiperidin-4-yl)sebacate, 55.0 g (0.427 mol) of 70% aqueous t-butyl hydroperoxide, 1.5 g (0.010 mol) of molybdenum trioxide, and 180 ml of decahydronaphthalene is heated at reflux for 4.5 hours until the red color disappears. Water is collected in a Dean-Stark trap. The molybdenum trioxide is removed by filtration and the filtrate stirred with a solution of 26 g of sodium sulfite in 500 ml of water to decompose unreacted t-butyl hydroperoxide. The two-phase mixture is diluted with ethyl acetate (200 ml) and the organic layer washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated at reduced pressure to obtain an oil. Purification by flash chromatography (silica gel, 19:1 heptane: ethyl acetate) affords 28.8 g (71% yield) of the title compound, a pale yellow oil.

Provenance & Evidence