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Benzylic oxidation

4 real reactions from the literature, on alkylbenzenes and pyridines. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Benzylic oxidation: 2-methylpyridine with KMnO4; H2O, Δ gives picolinic acid (the arenecarboxylic acid).

  2. Benzylic oxidation: chloro-(4-methylphenyl)mercury (an alkylbenzene) with 1) KMnO4; aq. NaOH, Δ; 2) HCl gives p-(chloromercuri)benzoic acid (the arenecarboxylic acid).

  3. Benzylic oxidation: 2-chlorotoluene (an alkylbenzene) with 1) KMnO4, H2O; 2) HCl gives 2-chlorobenzoic acid (the arenecarboxylic acid).

  4. Benzylic oxidation: 4-nitrotoluene (an alkylbenzene) with Na2Cr2O7; aq. H2SO4, Δ gives 4-nitrobenzoic acid (the arenecarboxylic acid).