Linoleic Acid → Oleyl linoleate

HRID 1752827Notes

Reaction equation

HRID 1752827 reaction equation
[C:1]([OH:20])(=[O:19])[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)Cl.OS(O)(=O)=O>[C:1]([O:20][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:19])[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 1

HCID 5280450Linoleic Acid

Product 1

HCID 6436476Oleyl linoleate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Oleyl linoleate was prepared by refluxing linoleic acid (1 g) and Oeyl alcohol (1 ml) in CH2Cl2 (20 ml) and concentrated H2SO4 (10 μl) overnight. The product was slightly pink and was purified by flash chromatography. The resultant Oeyl linoleate was subjected to the Simmons-Smith procedure described above to generate DCPLA-oleyl ester.

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-833bb285c7dd495e9b93d9aad39f8e43
Source dataset
uspto-grants-2015_10
Patent number
US09163032B2

Reaction notes

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