[syunchow]

Hi,

I'm having problem with the synthesis of p-cyanobenzoic acid. I started with p-tolunitrile, dissolved in sulfuric acid and added potassium dichromate with temperature maintained at 0 degree,  and then continue stirring at r.t for 48 h. The methyl group was oxidized to carboxylic acid group successfully but unfortunately the nitrile group has also been hydrolyzed into carboxylic acid. Is there a way to prevent this?

[OC pro]

According to this reference with Ruthenium trichloride: J. Org. Chem. 1986, p.2880.

[Åke]

Try: Levine, M.; Sedlecky, R. Preparation of p- and m-Aminomethylcyclohexylcarboxylic Acid. J. Org. Chem. 1959, 24, 115. http://pubs.acs.org/doi/abs/10.1021/jo01083a608

[syunchow]

Yayyy! I have solved this issues. Using the same condition, I kept the sulfuric solution at 0 degree, and instead of long reaction time, I shorted it to 5h - got my compound without nitrile hydrolysis 

[Vidya]

That's really great