Reaktion #54448

Reaktionsgleichung

stearic acid

N-chlorosuccinimide

→

2-chlorostearic acid

Ausbeute 70.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 50 ml 3-neck round bottom flask fitted with a condenser
2. 2
   Sonstigethermometer, and magnetic stirrer were placed
3. 3
   SonstigeThe flask was placed in a heating bath
4. 4
   Sonstigeset at 150° C
5. 5
   Temperaturduring heating
6. 6
   Sonstigea homogeneous liquid phase was formed
7. 7
   Sonstigea sudden exothermic reaction
8. 8
   TemperaturThe reaction mixture was cooled
9. 9
   Waschenthe resulting solution was washed thoroughly with dilute aqueous sodium chloride solution
10. 10
    SonstigeAfter drying
11. 11
    Sonstigeremoval of the chloroform
12. 12
    Sonstigethe residue was recrystallized from acetonitrile

Vorschrift

Into a 50 ml 3-neck round bottom flask fitted with a condenser, thermometer, and magnetic stirrer were placed 11.4 g (0.04 mole) stearic acid, 8.0 g (0.06 mole) N-chlorosuccinimide, 0.1 ml (0.0015 mole) chlorosulfonic acid, and 0.04 g (0.0002 mole) TCNQ. The flask was placed in a heating bath set at 150° C. The mixture was stirred during heating, and a homogeneous liquid phase was formed. The solution temperature continued to rise above that of the heating bath, and a sudden exothermic reaction occurred in which the reaction temperature increased to ca. 220° C. The reaction mixture was cooled and dissolved in chloroform, and the resulting solution was washed thoroughly with dilute aqueous sodium chloride solution. After drying and removal of the chloroform, the residue was recrystallized from acetonitrile to afford 8.9 g (70%) of 2-chlorostearic acid which was equivalent in purity to the product of Example I.

Quelle