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

HRID 1699593Notes

Reaction equation

HRID 1699593 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.S(=O)(=O)(O)O.[O:18]1CCC[CH2:19]1>>[CH3:19][O:18][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 4

HCID 1118Sulfuric AcidHCID 7612CyclopentadieneHCID 7923Maleic AnhydrideHCID 8028Tetrahydrofuran

Product 1

HCID 984652-Methyl bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylateYield 86%

Procedure

Cyclopentadiene (66 g) and tetrahydrofuran solvent (500 g) are charged in a reactor and the mixture is stirred homogeneously. To the reaction mixture, maleic anhydride (98 g) is added, and the resultant mixture is stirred at 0° C. for about 12 hours. Then, the mixture is filtered to remove the precipitate. To the resultant reactant, a 10% aqueous NaOH solution is added to carry out a hydrolysis reaction. The reactant is neutralized by using a 10% sulfuric acid solution. When reaction is completed, the resultant product is recovered by filtration and dried to obtain 150 g (yield: 86%) of mono-methyl cis 5-norbornene-endo-2,3-dicarboxylate.

Workup

  1. filtrationThen, the mixture is filtered
  2. customto remove the precipitate
  3. additionTo the resultant reactant, a 10% aqueous NaOH solution is added
  4. customa hydrolysis reaction
  5. customWhen reaction
  6. filtrationthe resultant product is recovered by filtration
  7. customdried

Sources & evidence

ORD record
ord-e35f00ae16324427ab13541b48f34e03
Source dataset
uspto-grants-2002_02
Patent number
US06348296B1

Reaction notes

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