"A Procedure for Quantitative Regioselective Nitration of Aromatic Hydrocarbons in the Laboratory"

André Cornélis, Lionel Delaude, André Gerstmans, and Pierre Laszlo

journal cover 
          source: Tetrahedron Letters
            year: 1988
          volume: 29
      first page: 5657
       last page: 5660
             doi: 10.1016/S0040-4039(00)80837-0
graphical abstract

Abstract: Aromatic hydrocarbons are nitrated by metallic nitrates impregnated on the K10 montmorillonite in the presence of acetic anhydride (Menke conditions). The influence on this stoichiometric reaction of the conditions (metallic cation; solvent; temperature) is studied. With toluene as the test molecule, the reaction is optimized to a 100% yield combined with a 8:1 para preference (79% para, 20% ortho, 1% meta).

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