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

HRID 2398922Notes

Reaction equation

HRID 2398922 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]>[Pd].C(OCC)(=O)C>[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 acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-norbornene-2-carboxylic acid (0.25 mole) in 100 ml. of ethyl acetate is hydrogenated over 5% palladium on carbon catalyst at 40 psi and 30°-50° C. The theoretical amount of hydrogen is absorbed exothermically within 0.5 hour. Removal of catalyst and solvent affords a residue of essentially pure norbornane-2-carboxylic acid, as indicated by infrared, NMR, and glpc analyses. The substituted acids are reduced readily in the same way.

Workup

  1. customThe theoretical amount of hydrogen is absorbed exothermically within 0.5 hour
  2. customRemoval of catalyst and solvent

Sources & evidence

ORD record
ord-264abb99afc54e3a9d49ed35b1861e46
Source dataset
uspto-grants-1977_05
Patent number
US04026712

Reaction notes

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