Stearic Acid → 2-Chlorooctadecanoic acid

Temperature

220 °C

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.

1. customInto a 50 ml 3-neck round bottom flask fitted with a condenser
2. customthermometer, and magnetic stirrer were placed
3. customThe flask was placed in a heating bath
4. customset at 150° C
5. temperatureduring heating
6. customa homogeneous liquid phase was formed
7. customa sudden exothermic reaction
8. temperatureThe reaction mixture was cooled
9. washthe resulting solution was washed thoroughly with dilute aqueous sodium chloride solution
10. customAfter drying
11. customremoval of the chloroform
12. customthe residue was recrystallized from acetonitrile

ORD record

ord-13cef6c6a2ec4cb5a26aed9bcc299f1f

Source dataset

uspto-grants-1979_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04148811