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Devise A Synthesis Of P-nitrobenzoic Acid From Tol ..

4-Methyl-3-nitrobenzoic acid

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p-nitrotoluene + hKMnO4/H3O+ -----> p-nitrobenzoic acid 2

SAMPLE SOLUTION(a) Of the two substituents in p-methylbenzoic acid, the methyl group is more activating and so controls the regioselectivity of electrophilic aromatic substitution. The position para to the ortho, para-directing methyl group already bears a substituent (the carboxyl group), and so substitution occurs ortho to the methyl group. This position is meta to the m-directing carboxyl group, and the orienting properties of the two substituents reinforce each other. The product is 4-methyl-3-nitrobenzoic acid.

PROBLEM 12.19Suggest an efficient synthesis of m-nitrobenzoic acid from toluene.
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Arelated problem concerns the synthesis of p-nitrobenzoic acid. Here, two metadirecting substituents are para to each other. This compound has been prepared from toluene according to the procedure shown:


Kamm, O., Matthews, A. O. 2003. p-Nitrobenzoic Acid. Organic Syntheses. 53.
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Reaction of di-n-butyltin oxide with 4,5-dimethoxy-2-nitrobenzoic acid yields the title compound which crystallizes as the usual dicarboxylatotetraorganodistannoxane dimer. Experimental details for the preparation and the structural characterization (by FTIR, NMR and single crystal XRD) are provided. The IR data shows that ligand acts in the bidentate manner. The crystal structure analysis of the compound reveals the presence of a centrosymmetric planar Sn2O2 unit connected to exocyclic Sn atom via two bidentate bridging carboxylate ligands. The remaining two carboxylate ligands are coordinated to the exocyclic Sn atom in the monodentate manner.

in industrial preparation of 4-nitrobenzoic acid;

Reaction of di-n-butyltin oxide with 4,5-dimethoxy-2-nitrobenzoic acid yields ..
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4-Nitrobenzoic acid | C7H5NO4 | ChemSpider
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  • Production 4-Nitrobenzoic acid is ..

    Answer to Starting from toluene, please propose a route for the synthesis of 2-bromo-4-nitrobenzoic acid

  • Para nitrobenzoic acid synthesis essay - …

    Structure, properties, spectra, suppliers and links for: 4-Nitrobenzoic acid, 62-23-7.

  • of steps is critical is synthesis of 4-nitrobenzoic acid …

    The product is 4-methyl-3-nitrobenzoic acid

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