tert-Butyl hydroperoxide → HCID 70374144, compound

Participants

Reaction Steps

A mixture of 25.0 g (0.052 mol) of bis(2,2,6,6-tetramethylpiperdin-4-yl) sebacate, 55.0 g (0.427 mol) of 70% aqueous tert-butyl hydroperoxide, 1.5 g (0.01 mol) of molybdenum trioxide and 180 ml of decahydronaphthalene (decalin) is heated at reflux for 4.5 hours till the red color disappears. Water is collected in a Dean-Stark trap. The molybdenum trioxide is removed by filtration and the filtrate is stirred with a solution of 26 g of sodium sulfite in 500 ml of water to decompose unreacted tert-butyl hydroperoxide. The 2-phase mixture is diluted with 200 ml of ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated at reduced pressure to give an oil. Purification by flash chromatography (silica gel, 19:1 heptane:ethyl acetate) affords 28.8 g (71% yield) of the title compound as a pale yellow oil.

Provenance & Evidence