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

HRID 258434

Reaction equation

HRID 258434 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].[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

3

Reactant 1

HCID 789495-Norbornene-2-carboxylic acid

Product 1

HCID 79113Bicyclo[2.2.1]heptane-2-carboxylic acidYield 100.8%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundSolvent

Procedure

38.8 g (269 mmol) of crude 5-norbornene-2-carboxylic acid was dissolved in 740 ml of solmix, 1.92 g of 5% palladium-carbon powder was added and the mixture was stirred for 17.5 hours under an atmosphere of hydrogen. The catalyst was filtered off, the solvent was distilled away, and 38.0 g of crude 2-norbornanecarboxylic acid was obtained. Crude yield: 100%.

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-a007d9d920d5419eb401b6a7ad62a729
Source dataset
uspto-grants-1993_11
Patent number
US05266728

Linked notes

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