Actually new subject: Mesitylene/Trimesic Acid -> Benzene

In summary, the conversation discusses the speaker's attempts to find a way to convert small carbon molecules (C2,C3) into benzene or its substituted derivatives. They mention the discovery of a trimerization process involving acetone to produce mesitylene, which can then be oxidized to trimesic acid. However, the speaker is unsure how to proceed from there to obtain benzene or its derivatives. They suggest the potential use of Hoffmann degradation and request for an "arrow" button in the editor.
  • #1
JeffEvarts
74
7
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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  • #2
Hoffmann degradation, maybe?
 

1. What is mesitylene/trimesic acid?

Mesitylene/trimesic acid is an organic compound that is also known as 1,3,5-trimethylbenzene or benzene-1,3,5-tricarboxylic acid. It is a colorless liquid at room temperature and is commonly used as a solvent in organic chemistry.

2. How is mesitylene/trimesic acid related to benzene?

Mesitylene/trimesic acid is a derivative of benzene, meaning that it is a similar compound with some slight chemical differences. It is derived from benzene through the addition of three carboxylic acid groups.

3. What are the properties of mesitylene/trimesic acid?

Mesitylene/trimesic acid has a boiling point of 164.7°C and a melting point of 72.4°C. It is soluble in organic solvents such as ethanol, ether, and acetone, but is not soluble in water. It is also flammable and should be handled with caution.

4. What are the uses of mesitylene/trimesic acid?

Mesitylene/trimesic acid is primarily used as a solvent in organic synthesis, as it is able to dissolve a wide range of compounds. It is also used in the production of dyes, plastics, and pharmaceuticals. Additionally, it can be used as a precursor to other chemicals, such as mesitaldehyde and mesityl oxide.

5. Is mesitylene/trimesic acid toxic or hazardous?

Mesitylene/trimesic acid is not considered to be highly toxic, but it can cause irritation to the skin, eyes, and respiratory system. It is also flammable and should be handled with caution in a well-ventilated area. It is important to follow proper safety precautions when handling this compound.

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