Reaktion #94255

Reaktionsgleichung

1,3-dimethyl-3-(t-butylperoxy)butyl alcohol

quinoline hydrochloride

isopropyl chloroformate

quinoline

quinoline

→

1,3-Dimethyl-3-(t-butylperoxy)butyl isopropyl carbonate

Lösungsmittel

pentane

pentane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeround-bottomed flask was equipped with a mechanical stirrer
2. 2
   Temperaturreflux condenser
3. 3
   workup.ADDITIONsurmounted by calcium chloride drying tube, addition funnel
4. 4
   Sonstigewas placed in a water bath at 221
5. 5
   Sonstige2 ° C
6. 6
   Sonstigedid not rise over 23° C
7. 7
   SonstigeReaction
8. 8
   workup.WAITthe reaction was completed after another 3 days
9. 9
   Sonstigewas withdrawn from the reaction mixture
10. 10
    workup.WAITto stand for 15 minutes
11. 11
    FiltrationThe quinoline hydrochloride was filtered off
12. 12
    Waschenwashed with 25 ml pentane which
13. 13
    workup.ADDITIONwas added to the pentane solution
14. 14
    WaschenThis solution was then successively washed with 25 ml
15. 15
    Trocknenportions of water, and finally dried over sodium sulfate
16. 16
    SonstigeAfter removal
17. 17
    Trocknenof drying agent and pentane
18. 18
    Sonstigewas obtained

Vorschrift

A four-necked 500 ml. round-bottomed flask was equipped with a mechanical stirrer, reflux condenser surmounted by calcium chloride drying tube, addition funnel and thermometer. A solution of 19 g. (0.1 mole) 1,3-dimethyl-3-(t-butylperoxy)butyl alcohol and 13.3 g (slightly over 0.1 mole) quinoline in 250 ml. pentane was placed in the flask which was placed in a water bath at 221/2 ° C. Then 12.3 g (0.1 mole) isopropyl chloroformate was added dropwise over 5 minutes; the temperature did not rise over 23° C. Reaction was not complete after 3 days. Another 3 g. of quinoline was added, and the reaction was completed after another 3 days as indicated by the fact that no further precipitate of quinoline hydrochloride formed when an aliquot of clean pentane solution was withdrawn from the reaction mixture and allowed to stand for 15 minutes. The quinoline hydrochloride was filtered off and washed with 25 ml pentane which was added to the pentane solution. This solution was then successively washed with 25 ml. of 7% hydrochloric acid, two 50 ml. portions of water, and finally dried over sodium sulfate. After removal of drying agent and pentane, a yield of 23.8 g. (86.4%) of material found to be 1,3-dimethyl-3-(t-butylperoxy)butyl isopropyl carbonate by infrared analysis, was obtained.

Quelle