Actually new subject: Mesitylene/Trimesic Acid -> Benzene

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SUMMARY

The discussion focuses on synthesizing benzene from small carbon molecules (C2, C3) through the trimerization of acetone to mesitylene, followed by oxidation to trimesic acid. The user highlights the challenge of converting trimesic acid to benzene due to its unexpectedly high melting point, which complicates base-catalyzed thermal decomposition. The inquiry seeks methods to safely and predictably convert either mesitylene or trimesic acid into benzene or its singly substituted derivatives.

PREREQUISITES
  • Understanding of organic synthesis techniques, specifically trimerization and oxidation reactions.
  • Familiarity with the properties and reactions of mesitylene and trimesic acid.
  • Knowledge of thermal decomposition processes in organic chemistry.
  • Experience with base-catalyzed reactions and their mechanisms.
NEXT STEPS
  • Research methods for the thermal decomposition of trimesic acid to benzene.
  • Investigate the Hoffmann degradation process and its applicability to the synthesis of benzene.
  • Explore alternative oxidizers for converting mesitylene to trimesic acid.
  • Study the synthesis of singly substituted benzene derivatives from mesitylene.
USEFUL FOR

Chemists, organic synthesis researchers, and students interested in advanced methods for synthesizing aromatic compounds from smaller carbon molecules.

JeffEvarts
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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?

P.S.
Might be wortwhile to add an "arrow" button to the editor... probably a common need.
 
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Hoffmann degradation, maybe?