Thionyl Chloride → Linoleoyl chloride

HRID 2249922Notes

Reaction equation

HRID 2249922 reaction equation
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]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride3×HCID 5280450Linoleic Acid

Product 1

HCID 9817754Linoleoyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-939664867f5f4b4a9e4bc5c819ea6d24
Source dataset
uspto-grants-2008_01
Patent number
US07314945B1

Reaction notes

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