Phosphorus pentachloride → Linoleoyl chloride

HRID 2395525Notes

Reaction equation

HRID 2395525 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].P(Cl)(Cl)(Cl)(Cl)[Cl:22]>C1C=CC=CC=1>[C:1]([Cl:22])(=[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 24819Phosphorus pentachlorideHCID 5280450Linoleic Acid

Product 1

HCID 9817754Linoleoyl chlorideYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 20.0 g of linolic acid in 70 ml of dry benzene was placed in a flask and kept swept therein with nitrogen for displacement of the entrapped air and 14.8 g of phosphorus pentachloride was added meanwhile thereto as divided in five split portions. The resultant reaction mixture was stirred at normal room temperature for 12 hours and then refluxed for two hours. Then, the reaction solution was distilled to expel benzene and the products of a secondary reaction, i.e. phosphoryl trichloride and hydrogen chloride and the residue was subjected to vacuum distillation to produce 14.0 g of linolic acid chloride (boiling point 155° C./1.5 mmHg; yield 76%).

Workup

  1. customsplit portions
  2. customThe resultant reaction mixture
  3. temperaturerefluxed for two hours
  4. distillationThen, the reaction solution was distilled
  5. customthe products of a secondary reaction, i.e. phosphoryl trichloride and hydrogen chloride
  6. distillationthe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-b37f93eeb6b6472d8b97733e90652630
Source dataset
uspto-grants-1996_02
Patent number
US05489303

Reaction notes

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