Diethyl fumarate → Diethyl Maleate
Reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:7][CH3:8])=[O:5]>CC1C=CC(C)=CC=1>[C:4]([O:6][CH2:7][CH3:8])(=[O:5])/[CH:3]=[CH:2]\[C:1]([O:10][CH2:11][CH3:12])=[O:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 500 ml four-necked flask were charged 305 mmol (52.5 g) of diethyl fumarate obtained by isomerization of diethyl maleate and 400 ml of p-xylene. The flask was provided with a thermometer, a dropping funnel and a condenser, and put in an oil bath. While maintaining the temperature at 135° C. under stirring with a magnetic stirrer and refluxing under a flow of nitrogen, a solution of 35 mmol (5.8 g) of AIBN (2,2-azobisisobutyronitrile) in p-xylene was added dropwise over 11 hours. The heating and refluxing were continued for further 19 hours. The solvent and unreacted reactant were then distilled off under reduced pressure to obtain 49 g of a reaction product with a yield of 94%.
Sources & evidence
- ORD record
- ord-866f450218814a53b7edbfa2dbb20c3e
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05798054
Reaction notes
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