反应详情

温度

151 °C

A 2-phase mixture of 85.7 g (0.666 mol) of 70% aqueous tert-butyl hydroperoxide, 200 ml of n-nonane and 15 g of sodium chloride is agitated in a separatory funnel. The organic layer is dried over anhydrous magnesium sulfate. A mixture of 40.0 g (0.0832 mol) of bis-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate and the tert-butyl hydroperoxidenonane solution is heated to reflux (151° C.) under a nitrogen atmosphere. To this mixture is added over a 10-minute period, a solution of 5.0 g of titanium tetrabutoxide in 50 ml of nonane. The reaction mixture turns red. Water is collected in a Dean Stark trap. The reaction mixture is heated at reflux for 17 hours. Another 5.0 g of titanium tetrabutoxide is added, and the reaction mixture is heated at reflux for an additional 7 hours. Solids are removed by filtration, and the filtrate is concentrated under reduced pressure. The crude red oil obtained is purified by chromatography (Waters Prep 500A HPLC; 29:1 heptane:ethyl acetate) to give 3.6 g (6% yield) or the title compound as a light yellow oil.

1. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
2. additionTo this mixture is added over a 10-minute period
3. customWater is collected in a Dean Stark trap
4. temperatureThe reaction mixture is heated
5. temperatureat reflux for 17 hours
6. additionAnother 5.0 g of titanium tetrabutoxide is added
7. temperaturethe reaction mixture is heated
8. temperatureat reflux for an additional 7 hours
9. customSolids are removed by filtration
10. concentrationthe filtrate is concentrated under reduced pressure
11. customThe crude red oil obtained
12. customis purified by chromatography (Waters Prep 500A HPLC; 29:1 heptane:ethyl acetate)
13. customto give 3.6 g (6% yield)