Реакция #54448

Уравнение реакции

stearic acid

N-chlorosuccinimide

→

2-chlorostearic acid

Выход 70.0%

Растворители

chloroform

Условия реакции

Обработка

1. 1
   ДругоеInto a 50 ml 3-neck round bottom flask fitted with a condenser
2. 2
   Другоеthermometer, and magnetic stirrer were placed
3. 3
   ДругоеThe flask was placed in a heating bath
4. 4
   Другоеset at 150° C
5. 5
   Температураduring heating
6. 6
   Другоеa homogeneous liquid phase was formed
7. 7
   Другоеa sudden exothermic reaction
8. 8
   ТемператураThe reaction mixture was cooled
9. 9
   Промывкаthe resulting solution was washed thoroughly with dilute aqueous sodium chloride solution
10. 10
    ДругоеAfter drying
11. 11
    Другоеremoval of the chloroform
12. 12
    Другоеthe residue was recrystallized from acetonitrile

Методика

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.

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