Ethanol → Monoethyl fumarate

HRID 1656554Notes

Reaction equation

HRID 1656554 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.S(Cl)(Cl)=O.C(Cl)(Cl)(Cl)Cl.[CH2:17]([OH:19])[CH3:18]>>[C:4]([O:19][CH2:17][CH3:18])(=[O:5])/[CH:3]=[CH:2]/[C:1]([OH:6])=[O:7]

Participants

5

Reactant 4

HCID 702EthanolHCID 5943Carbon TetrachlorideHCID 7923Maleic AnhydrideHCID 24386Thionyl Chloride

Product 1

HCID 5358902Monoethyl fumarate

Procedure

Maleic anhydride (100.0 g, 1.02 mole) was dissolved in anhydrous ethanol (60 ml, excess) by heating the mixture in an erlenmeyer flask on a steam bath. Thionyl chloride (1.0 ml) was added using a syringe and the mixture heated with stirring for ten minutes. To the turbid mixture was added carbon tetrachloride (100 ml) and the liquid quickly filtered through a Buchner funnel having a coarse glass frit. The solid was discarded. The filtrate was allowed to cool during which the time the ethyl hydrogen fumarate product (92 g, 63%) crystallized.

Workup

  1. temperatureby heating the mixture in an erlenmeyer flask on a steam bath
  2. temperaturethe mixture heated
  3. filtrationthe liquid quickly filtered through a Buchner funnel
  4. temperatureto cool during which the time the ethyl hydrogen fumarate product (92 g, 63%)
  5. customcrystallized

Sources & evidence

ORD record
ord-0b53c942f9da4a76a414a75b070d6e19
Source dataset
uspto-grants-1993_10
Patent number
US05254667

Reaction notes

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