Sciencemadness Discussion Board

Nitration of benzoic acid

vmelkon - 20-3-2014 at 07:53

I'm not very experienced in organic chemistry.

I prepared my benzoic acid from toluene oxidation.
Is it possible to nitrate benzoic acid?
The problem is that it is a solid.

From what I read, they nitrate toluene (I'm interested in the para position), then they oxidize the para-nitrotoluene to para-nitrobenzoic acid.

Metacelsus - 20-3-2014 at 08:00

It is possible. However, nitration of benzoic acid will form the meta isomer. To get the para isomer, the toluene route is best.

Galinstan - 20-3-2014 at 08:23

i agree with Cheddite cheese although if you nitrate toluene you will get a mixture of ortho AND para nitro-toluene which will have to be separated before you oxides the methyl group to yield your carboxylic acid and the temperature kept low to only get mono nitration.