[roc]

I have been unsuccessful in finding a suitable way to improve the yield in my Methyl-nitrobenzoate lab.  I got approximately 63.8 %.  The experiment was catalyzed by sulfuric acid and nitric acid with methyl benzoate.   As of now im concluding that its perhaps to first nitrate a benzene.  Then convert that to add an amino thus one can easily add the ester through friedel crafts acylation.  Then revert the amino group into N02.  But this is all theoretical and doesn't seem all that financially good.  I am hoping that some one here can help point me in I'he right direction.

[Honclbrif]

Nitro and carboxyl are both deactivators, therefore m-directing. If you reduce the nitro to an amine, you will surely get a more active substrate, but the directing effects will be all wrong.

[pharmacykat]

Whats the orientation of the methylbenzoate group with respect to the nitro?

[Honclbrif]

Another issue is that converting a nitro to an amine is pretty easy, but converting an amine to a nitro is harder. Doing it without trashing everything in your molecule which can be oxidized is much, much harder.

Could you do anything with mononitrotoluene?

[pharmacykat]

according to the internet, not many people are getting over 64%