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

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Reaction Steps

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.

Provenance & Evidence