Ethanol → 2-Methyl bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylate

HRID 841000Notes

Reaction equation

HRID 841000 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]1(=[O:12])[O:11][C:9](=[O:10])[CH:8]=[CH:7]1.[CH2:13]([OH:15])C>O1CCCC1>[CH3:13][O:15][C:9]([CH:8]1[CH:7]([C:6]([OH:11])=[O:12])[CH:4]2[CH:5]=[CH:1][CH:2]1[CH2:3]2)=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 7612CyclopentadieneHCID 7923Maleic Anhydride

Product 1

HCID 984652-Methyl bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a reactor, cyclopentadiene (66 g) was charged, and tetrahydrofuran solvent (500 g) and maleic anhydride (98 g) were added thereto, and the mixture was stirred homogeneously. To the reaction mixture, pure ethanol (500 g) was added and the reaction was carried out with stirring at 50° C. for 8 hours. when the reaction was completed, the solvent was removed by using a rotary evaporator, and the residue was distilled under reduced pressure to obtain 156 g (yield: 87%) of mono-methyl cis-5-norbornene-endo-2, 3-dicarboxylate represented by chemical formula XI.

Workup

  1. stirringwith stirring at 50° C. for 8 hours
  2. customthe solvent was removed
  3. customa rotary evaporator
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-9750472aecbb49e69fe4b0c66fdcdf22
Source dataset
uspto-grants-2002_04
Patent number
US06369181B1

Reaction notes

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