Isodecanol → (2E)-2-Bromo-2-butenedioic acid

HRID 1656666Notes

Reaction equation

HRID 1656666 reaction equation
[Br:1][C:2]1[C:3]([O:5][C:6](=[O:8])[CH:7]=1)=[O:4].C([OH:19])CCCCCCC(C)C>C1(C)C=CC=CC=1>[Br:1]/[C:2](=[CH:7]/[C:6]([OH:5])=[O:8])/[C:3]([OH:19])=[O:4]

Participants

4

Reactant 2

HCID 32898IsodecanolHCID 800273-Bromo-2,5-furandione

Product 1

HCID 5358119(2E)-2-Bromo-2-butenedioic acidYield 260.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bromomaleic anhydride (19.5 g), isodecanol (69.5 g) p-toluene sulphonic acid (2 g) and toluene (70 ml) were stirred and boiled under reflux below a Dean-Stark trap of volume 15 ml for 2.5 hours. The solution was then cooled with petroleum ether and the petroleum ether solution was washed with water. The solvent and excess isodecanol were distilled under reduced pressure, finally at 100°/0.2 mm of mercury pressure, leaving the bis(isodecyl)ester of bromomaleic acid (56 g) as an oil with an estimated purity by gas chromatography of 96%.

Workup

  1. temperatureunder reflux below a Dean-Stark trap of volume 15 ml for 2.5 hours
  2. washthe petroleum ether solution was washed with water
  3. distillationThe solvent and excess isodecanol were distilled under reduced pressure, finally at 100°/0.2 mm of mercury pressure

Sources & evidence

ORD record
ord-5893f884ce5b44b6bbe4d8042f3cff83
Source dataset
uspto-grants-1993_10
Patent number
US05254695

Reaction notes

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