Oxalyl chloride → Linoleoyl chloride

HRID 1005615

Reaction equation

HRID 1005615 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)(=O)C([Cl:24])=O>CCCCCC>[C:1]([Cl:24])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 5280450Linoleic Acid

Product 1

HCID 9817754Linoleoyl chlorideYield 100.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Linoleic acid (100 g; purity 95%, 356 mmoles) was added dropwise over a period of 0.5 hours to a stirred mixture of oxalyl chloride (42 ml; 481 mmoles) and of hexane (120 ml) under nitrogen. After the addition the mixture was refluxed for 1.5 hours and then evaporated under reduced pressure (60° C.; 0.5 mm Hg) to give 107 grams of linoleoyl chloride as an oil.

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas refluxed for 1.5 hours
  3. customevaporated under reduced pressure (60° C.; 0.5 mm Hg)

Sources & evidence

ORD record
ord-56df09f444e64accbce9e0c7617445eb
Source dataset
uspto-grants-2000_04
Patent number
US06054599

Linked notes

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