Sodium Chloride → Di-(1-nonyloxy-2,2,6,6-tetramethylpiperidin-4-yl) Sebacate

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A 2-phase mixture of 85.7 g (0.666 mol) of 70% aqueous tert-butyl hydroperoxide, 150 ml of n-nonane and 10 g of sodium chloride is agitated in a separatory funnel. The organic layer is dried over anhydrous magnesium sulfate. The magnesium sulfate is removed by filtration and then washed rinsed with 50 ml of n-nonane. The nonane rinse solution is then added to the original filtrate. A mixture of 40.0 g (0.083 mol) of bis-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, the combined hydroperoxide-nonane solution and an additional 50 ml of nonane is heated at reflux in a nitrogen atmosphere for 18 hours. The reaction mixture is still red at the end of this period. The nonane solvent is evaporated under reduced pressure and the residue is purified by chromatography (Waters Prep 500A HPLC, 29:1, heptane:ethyl acetate) to obtain 17.2 g (27% yield) of the title compound as a clear, colorless oil.

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