5-Norbornene-2-carboxylic acid → Bicyclo[2.2.1]heptane-2-carboxylic acid

HRID 258442

Reaction equation

HRID 258442 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([OH:10])=[O:9]>C(O)C.[C].[Pd]>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 789495-Norbornene-2-carboxylic acid

Product 1

HCID 79113Bicyclo[2.2.1]heptane-2-carboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

15.7 g (110 mmol) of crude 5-norbornene-2-carboxylic acid was dissolved in 300 ml of ethanol, 1.55 g of 5% palladium-carbon powder was added, and the mixture was stirred under an atmosphere of hydrogen for 24 hours. After the catalyst was filtered off, the solvent was distilled off, and 14.5 g of crude 2-norbornanecarboxylic acid was obtained. Crude yield: 94%.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-450580ae0ff94758a4f9e307b836054b
Source dataset
uspto-grants-1993_11
Patent number
US05266728

Linked notes

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