Reaktion #345412

Reaktionsgleichung

2-(3-hydroxypropyl)-1-cyclododecanone

acetic acid

sulphuric acid

→

14a-hydroperoxy-cyclododeca[b]-pyran

Ausbeute 84.5%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 4-neck flask equipped with mechanical stirring, an inlet funnel
2. 2
   TemperaturThe reaction mixture was cooled to 0° C.
3. 3
   Sonstige10 ml of 70% oxygenated water
4. 4
   workup.ADDITIONwere added
5. 5
   Sonstigerose to 7° C
6. 6
   workup.STIRRINGstirring
7. 7
   workup.WAITwas continued for 15 min at 0° C
8. 8
   FiltrationThe formed precipitate was filtered
9. 9
   Waschenwashed with water
10. 10
    Sonstige62.0 G of wet product were thus obtained which
11. 11
    Sonstigeafter drying

Vorschrift

A 4-neck flask equipped with mechanical stirring, an inlet funnel, a thermometer, a condenser and kept under nitrogen, was charged with 30 g (125 mmol) of 2-(3-hydroxypropyl)-1-cyclododecanone and 137.5 g (2.29 mol) of glacial acetic acid. The mixture was stirred at room temperature until it became homogeneous. A cooled mixture of water (12.5 g) and a 50% aqueous solution of sulphuric acid (12.5 g) was then added. The reaction mixture was cooled to 0° C. and then 10 ml of 70% oxygenated water were added thereto dropwise over 15 min; the temperature rose to 7° C. Once the introduction was completed, stirring was continued for 15 min at 0° C. The formed precipitate was filtered, washed with water and then with diluted aqueous NaHCO3. 62.0 G of wet product were thus obtained which, after drying, provided 25.6 g (yield 80%) of 14a-hydroperoxy-cyclododeca[b]-pyran which was used in the following step. M. p.: 104°-106° C.

Quelle