Reaktion #543367

Reaktionsgleichung

triethylamine

1,3-Propanediol

erucoyl chloride

diisopropyl ether

HCl

→

Erucoyl-1,3-propanediol

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequilibrated at 20° C. in a water bath
2. 2
   Sonstigedoes not exceed 30° C
3. 3
   workup.ADDITIONThe dropwise addition
4. 4
   workup.STIRRINGAfter vigorous shaking
5. 5
   Sonstigephase separation
6. 6
   Waschenthe upper ether phase is washed once again with 1% NaCl solution
7. 7
   Sonstigeevaporated in vacuo at 45° C
8. 8
   Temperaturcooled to −20° C
9. 9
   FiltrationThe white crystals are filtered off with suction
10. 10
    Sonstigedried in vacuo

Vorschrift

1,3-Propanediol, 153 g (MW 76.1; 2 mol) is dissolved in 1 l of THF and, after addition of 60 g of triethylamine (MW 101.2, 0.6 mol) and 7.3 g of 4-dimethylaminopyridine (MW 122.2, 0.06 mol), equilibrated at 20° C. in a water bath. While stirring continuously, 178 g of erucoyl chloride (MW 357.0; 0.5 mol) in 500 ml of THF are slowly added dropwise so that the temperature in the reaction mixture does not exceed 30° C. The dropwise addition is followed by warming at 30° C. for 30 minutes and then addition of 1.5 l of diisopropyl ether and 1.5 l of 1N HCl. After vigorous shaking and phase separation, the upper ether phase is washed once again with 1% NaCl solution and evaporated in vacuo at 45° C. The residue is taken up in 2 l of hexane and cooled to −20° C. The white crystals are filtered off with suction and dried in vacuo. The yield of pure erucoyl-1,3-propanediol is 123 g (MW 396.7; 62%). The substance is pure by thin-layer chromatography (Rf value 0.3 in ether/pentane/acetic acid 200/200/2 parts by volume).

Quelle