Reaktion #80666

Reaktionsgleichung

4-acetoxy-2,2,6,6-tetramethylpiperidine

cyclohexane

water

→

1-Cyclohexyloxy-2,2,6,6-tetramethyl-4-acetoxypiperidine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefitted with magnetic stirrer
2. 2
   Extraktion154 g (1.2 mol) of an aqueous 70% solution of t-butyl hydroperoxide are extracted three times with 35 ml of cyclohexane in each case
3. 3
   Trocknenthe organic phase is dried over sodium sulfate
4. 4
   TemperaturThe reaction mixture is warmed
5. 5
   Temperaturto reflux
6. 6
   workup.ADDITIONthe t-butyl hydroperoxide solution is added dropwise over the course of 2 hours
7. 7
   Sonstigeis held at the reflux temperature overnight
8. 8
   Filtrationthe catalyst is filtered off
9. 9
   workup.ADDITIONIce is added
10. 10
    workup.ADDITIONa little sodium sulfite is added in order
11. 11
    Sonstigeto destroy the excess hydroperoxide
12. 12
    Sonstigethe organic phase is then separated off
13. 13
    Waschenwashed with water
14. 14
    Trocknendried over sodium sulfate
15. 15
    Sonstigethe solvent is removed on a Rotavap

Vorschrift

60 g (301 mmol) of 4-acetoxy-2,2,6,6-tetramethylpiperidine are dissolved in 300 ml of cyclohexane under nitrogen in a 1.5 l sulfonation flask fitted with magnetic stirrer, water separator, thermometer and dropping funnel. 4.3 g (30 mmol) of molybdenum oxide are added. 154 g (1.2 mol) of an aqueous 70% solution of t-butyl hydroperoxide are extracted three times with 35 ml of cyclohexane in each case, and the organic phase is dried over sodium sulfate and transferred into the dropping funnel. The reaction mixture is warmed to reflux, and the t-butyl hydroperoxide solution is added dropwise over the course of 2 hours. After a further 2 hours, the elimination of water is complete. The mixture is held at the reflux temperature overnight and is then cooled to 25° C., and the catalyst is filtered off. Ice is added, a little sodium sulfite is added in order to destroy the excess hydroperoxide, and the organic phase is then separated off, washed with water and dried over sodium sulfate, and the solvent is removed on a Rotavap.

Quelle