Reaktion #4603

Reaktionsgleichung

tert.butyl alcohol

epichlorohydrin

sodium hydroxide

pyrrolidine

→

oil

Ausbeute 82.6%

1-[3-(1,1-Dimethylethoxy)-2-hydroxypropyl]pyrrolidine

Ausbeute 82.6%

Lösungsmittel

water

—

xylenes

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeimmediately exothermed to about 100° C
2. 2
   workup.STIRRINGThe reaction mixture was stirred at about 50° C. for 1.5 hrs
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGThe reaction mixture was stirred
5. 5
   Temperaturheated
6. 6
   Temperaturto reflux for 1 hr
7. 7
   TemperaturThe reaction mixture was cooled to RT
8. 8
   Extraktionextracted with ether
9. 9
   TrocknenThe ether soluble portion was dried
10. 10
    Einengenconcentrated in vacuo

Vorschrift

A mixture of 100.0 g (1.35 m) of tert.butyl alcohol and 51.4 g (1.35 m) of epichlorohydrin in 240 ml of xylenes was stirred and heated to 50° C. Tin (IV) chloride (3.5 g; 1.6 ml; 0.031 m) was added all at once and the reaction mixture immediately exothermed to about 100° C. The reaction mixture was stirred at about 50° C. for 1.5 hrs then cooled to 5° C. while a mixture of 97 g of 50% sodium hydroxide solution and 195 g of ice was added followed by 115.1 g (1.62 m) of pyrrolidine. The reaction mixture was stirred and heated to reflux for 1 hr. The reaction mixture was cooled to RT, diluted with 1 liter of water and extracted with ether. The ether soluble portion was dried and concentrated in vacuo to give 92.4 g of oil which was distilled at 97.5°-97° C./0.075 mm to yield 63.85 g of the title compound.

Quelle