Cyclopentadiene → 826-62-0

HRID 1731209Notes

Reaction equation

HRID 1731209 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>>[CH2:2]1[CH:1]2[CH:7]3[C:6](=[O:12])[O:11][C:9](=[O:10])[CH:8]3[CH:3]1[CH:4]=[CH:5]2

Participants

3

Reactant 2

HCID 7612CyclopentadieneHCID 7923Maleic Anhydride

Product 1

HCID 13223826-62-0Yield 25%

Procedure

The Diels-Alder adduct from cyclopentadiene and maleic anhydride, endo-cis-5-norbornene-2,3-dicarboxylic anhydride, m.p. 165° C, was heated at 220° C. for 4 hours. On cooling, the product solidified with a melting point of 101° C. The crude reaction product was recrystallized from benzene three times to isolate exo-cis-5-norbornene-2,3-dicarboxylic anhydride, m.p. 141° C., in 25% yield.

Workup

  1. temperatureOn cooling
  2. customThe crude reaction product
  3. customwas recrystallized from benzene three times

Sources & evidence

ORD record
ord-2d0eb41bc4f944f8aebf83477306905d
Source dataset
uspto-grants-1976_11
Patent number
US03995099

Reaction notes

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