Acrylic Acid → 5-Norbornene-2-carboxylic acid

HRID 1699592Notes

Reaction equation

HRID 1699592 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]([OH:10])(=[O:9])C=C.O1CC[CH2:13][CH2:12]1>>[CH:2]12[CH2:1][CH:5]([CH:12]=[CH:13]1)[CH2:4][CH:3]2[C:6]([OH:10])=[O:9]

Participants

4

Reactant 3

HCID 6581Acrylic AcidHCID 7612CyclopentadieneHCID 8028Tetrahydrofuran

Product 1

HCID 789495-Norbornene-2-carboxylic acidYield 79.7%

Procedure

Cyclopentadiene (66 g) and acrylic acid (86 g) are charged in a reactor and the mixture is dissolved in tetrahydrofuran solvent (500 g). The resultant mixture is reacted at 30° C. for about 24 hours. Then, the solvent is removed by using a rotary evaporator, and the residue is distilled under reduced pressure to obtain 110 g (yield: 71%) of 5-norbornene-2-carboxylic acid.

Workup

  1. customThen, the solvent is removed
  2. customa rotary evaporator
  3. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-41927ea27be14584bb929c33245ff7a4
Source dataset
uspto-grants-2002_02
Patent number
US06348296B1

Reaction notes

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