Stearic Acid → 2-Chlorooctadecanoic acid

HRID 26170

反応式

HRID 26170 の反応式
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Cl:21]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.ClS(O)(=O)=O.C1C(=C(C#N)C#N)C=CC(=C(C#N)C#N)C=1>[Cl:21][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:1]([OH:20])=[O:19]

参加物

6

反応物 2

HCID 5281Stearic AcidHCID 31398Chlorosuccinimide

生成物 1

HCID 130597772-Chlorooctadecanoic acid収率 70%

試薬・触媒・溶媒 3

HCID 24638Chlorosulfonic acid触媒HCID 73697Tetracyanoquinodimethane触媒HCID 6212Chloroform溶媒

反応条件

温度
220 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-13cef6c6a2ec4cb5a26aed9bcc299f1f
出典データセット
uspto-grants-1979_04
特許番号
US04148811

関連ノート

読み込み中…