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Actually new subject: Mesitylene/Trimesic Acid -> Benzene

  1. Oct 25, 2016 #1
    I have been trying to come up with a way to get from some small carbon molecules (C2,C3) to benzene, or its singly substituted friends like phenol, aniline, or benzoic acid.

    I stumbled upon a trimerization of acetone to mesitylene (3 C3H7O --> C6H3(CH3)3 + 3H2O) which can be oxidized (via nitric acid, or presumably other oxidizers) to trimesic acid (tricarboxil benzene)

    This gets me tantalizingly close to my target, and I had assumed (oops) that you could do a slow and simple base-catalyzed thermal decomp of trimesic acid as can be doneld with benzoic acid, but the trimesic acid has a higher (stable) melting point than I had expected.

    Does anyone know of a way to proceed from either mesitylene or trimesic acid safely and predictably to benzene or a singly-substituted benzene?

    Might be wortwhile to add an "arrow" button to the editor... probably a common need.
  2. jcsd
  3. Oct 27, 2016 #2


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    Science Advisor

    Hoffmann degradation, maybe?
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