Thionyl Chloride → Linoleoyl chloride

HRID 1788308

Reaktionsgleichung

Reaktionsgleichung von HRID 1788308
S(Cl)([Cl:3])=O.[C:5]([OH:24])(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O>[C:5]([Cl:3])(=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

4

Edukt 2

HCID 24386Thionyl Chloride3×HCID 5280450Linoleic Acid

Produkt 1

HCID 9817754Linoleoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 9.35 ml (128 mmol) of thionyl chloride, and a water condenser, is placed 24.90 ml (80 mmol) of linoleic acid. Addition of the thionyl chloride is completed with heating to about 40° C. over the course of about 40 minutes. When addition of the thionyl chloride is complete the mixture is heated and stirred for an additional 50 minutes. The water condenser is then replaced with a distillation side arm condenser and the crude mixture is distilled. The crude distillate in the receiving flask is then fractionally distilled to obtain the acyl chloride, (9Z,12Z)-octadeca-9,12-dienoyl chloride.

Aufarbeitung

  1. customIn a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer
  2. customfixed with a separatory funnel
  3. temperatureis heated
  4. distillationthe crude mixture is distilled
  5. distillationThe crude distillate in the receiving flask is then fractionally distilled

Quellen und Nachweise

ORD-Eintrag
ord-80af1d69e9954dfa913604ecbf08a2fe
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511162B2

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