Maleic Anhydride → 1,4-Di(9Z)-9-octadecen-1-yl (2Z)-2-butenedioate

HRID 1939846Notes

Reaction equation

HRID 1939846 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([OH:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31](S(O)(=O)=O)=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[C:4]([O:6][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:28][CH3:38])(=[O:5])/[CH:3]=[CH:2]\[C:1]([O:26][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:7]

Participants

5

Reactant 3

HCID 7923Maleic AnhydrideHCID 521998p-Toluenesulfonic acid monohydrateHCID 5284499Oleyl Alcohol

Product 1

HCID 208387301,4-Di(9Z)-9-octadecen-1-yl (2Z)-2-butenedioate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of maleic anhydride (88.25 g), oleyl alcohol (483.28 g), p-toluenesulfonic acid monohydrate (8.56 g), and toluene (650 mL) was refluxed under nitrogen. Water was separated from the distillate in a Barrett distilling receiver. When the theoretical amount of water (17 g) was collected, the heating was stopped and the toluene removed in vacuo on a rotary evaporator. The product was a brown oil (532 g) and was used in Example 4 without further purification.

Workup

  1. temperaturewas refluxed under nitrogen
  2. customWater was separated from the distillate in a Barrett
  3. distillationdistilling receiver
  4. customWhen the theoretical amount of water (17 g) was collected
  5. customthe toluene removed in vacuo on a rotary evaporator
  6. customwas used in Example 4 without further purification

Sources & evidence

ORD record
ord-f46dbf7ed1304d70afbb2d3ac6aedd00
Source dataset
uspto-grants-1997_12
Patent number
US05698016

Reaction notes

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