Acrylic Acid → 5-Norbornene-2-carboxylic acid

HRID 1276019Notes

Reaction equation

HRID 1276019 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]([OH:10])(=[O:9])C=C.[CH2:11]1COC[CH2:12]1>>[CH:2]12[CH2:1][CH:5]([CH:11]=[CH:12]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 86 g of acrylic acid were dissolved in 500 g of THF solvent. After the reaction at 30° C. for 24 hours, the solvent and excess acrylic acid were removed by rotary evaporator. The residue was distilled under reduced pressure to obtain 110 g of 5-norbornene-2-carboxylic acid as a mixture of endo and exo (yield: 71%). NMR spectral data of the resulting compound (20) is shown in FIG. 3.

Workup

  1. customAfter the reaction at 30° C. for 24 hours
  2. customthe solvent and excess acrylic acid were removed by rotary evaporator
  3. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-7c9280c491ab4ed390c90b5e1423d06b
Source dataset
uspto-grants-2000_12
Patent number
US06165672

Reaction notes

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