Maleic Anhydride → Bicyclo(2.2.2)oct-5-ene-2,3-dicarboxylic Anhydride

HRID 583437Notes

Reaction equation

HRID 583437 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[CH:10]12[CH2:11][CH2:12][CH:13]([CH:8]=[CH:9]1)[CH:2]1[C:1]([O:6][C:4](=[O:5])[CH:3]21)=[O:7]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 116051,3-Cyclohexadiene

Product 1

HCID 220977Bicyclo(2.2.2)oct-5-ene-2,3-dicarboxylic AnhydrideYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of maleic anhydride (10.30 g, 105.0 mmol) in toluene (100 mL) was added 1,3-cyclohexadiene (8.41 g, 105.0 mmol). The mixture was heated to reflux temperature and allowed to react for 3 hrs. After cooling to room temperature, the solvent was evaporated and the remaining solid was recrystallized from EtOAc/hexane to yield pure bicyclo[2.2.2]oct-5-en-2,3-dicarboxylic anhydride as colorless crystals: 14.11 g (75% yield), mp=117° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature
  3. customto react for 3 hrs
  4. customthe solvent was evaporated
  5. customthe remaining solid was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-3a80590718de4a1d92027ccc5b3b92e5
Source dataset
uspto-grants-1999_07
Patent number
US05929146

Reaction notes

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