Reaction #4602

Reaction equation

pyrrolidine

sodium hydroxide

epichlorohydrin

neopentyl alcohol

→

oil

Yield 84.1%

α-[(2,2-Dimethylpropoxy)methyl]-1-pyrrolidineethanol

Yield 84.1%

Conditions

Workup

1. 1
   Otherrose to about 60° C.
2. 2
   workup.WAITthen exothermed to about 130° C. in a few seconds
3. 3
   Otherreceded to about 40° C.
4. 4
   workup.STIRRINGThe reaction mixture was stirred
5. 5
   TemperatureAfter cooling the reaction mixture to RT
6. 6
   workup.ADDITIONwas added
7. 7
   workup.STIRRINGThe reaction mixture was stirred
8. 8
   Temperatureheated to 90° C. for 0.5 hr
9. 9
   Temperaturethen cooled to RT
10. 10
    OtherThe reaction mixture was partitioned between 400 ml of ice water and 400 ml of ether
11. 11
    OtherThe organic layer was dried
12. 12
    Concentrationconcentrated in vacuo

Procedure

To a stirred mixture of 92.53 g (1.0 m) of epichlorohydrin and 88.15 g (1.0 m) of neopentyl alcohol was added 0.26 g (0.001 m) of stannic chloride. The reaction temperature rose to about 60° C. then exothermed to about 130° C. in a few seconds. The reaction mixture was stirred until the temperature receded to about 40° C. then 71.12 g (1.0 m) of pyrrolidine was added. The reaction mixture was stirred and heated to about 95° C. for 1 hr. After cooling the reaction mixture to RT, a mixture of 80 g of 50% sodium hydroxide solution and 80 g of ice was added. The reaction mixture was stirred and heated to 90° C. for 0.5 hr then cooled to RT. The reaction mixture was partitioned between 400 ml of ice water and 400 ml of ether. The organic layer was dried and concentrated in vacuo to give 181 g of oil. The oil was distilled (89°-115° C. at 0.25 mm) to give 136 g of oil that crystallized on standing, 99.1% pure by g.c.

Source