m-nitrobenzoic acid from benzene?

1 Answer
Truong-Son N.
Mar 23, 2018

Here's one way to do it below... Another way to do it is three steps:

  1. #"CH"_3"Br"#, #"FeBr"_3# (forming toluene)
  2. #"KMnO"_4//"OH"^(-)# (forming benzoic acid)
  3. #"HNO"_3//"H"_2"SO"_4# (forming the product)

I'll leave it to you to draw the intermediates.

#"Br"_2# catalyzed by #"FeBr"_3# brominates benzene. It's a classic aromatic bromination.

Then a Grignard reagent can be made... as long as there's limited moisture.

It'll then react with #"CO"_2(g)# in the air (or it can be expedited by using dry ice), and the product can be acidified to form benzoic acid.

Then the last step is a standard nitration you could do in lab, forming mostly the meta product, but a small amount of para and ortho side product.

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