To prepare 9,10-anthraquinone from benzene via benzoylbenzoic acid.
Answer (2)
To prepare 9,10-anthraquinone from benzene via benzoylbenzoic acid, follow these general steps involved in the synthetic pathway:
Friedel-Crafts Acylation of Benzene :
Start with benzene as your base compound.
Perform a Friedel-Crafts acylation to introduce an acyl group using an acid chloride (such as acetyl chloride) and a Lewis acid catalyst like aluminum chloride (AlCl₃).
This step forms acetophenone.
Form Benzoylbenzoic Acid :
Conduct a carboxylation reaction by treating the product with carbon dioxide in the presence of a base, forming benzoylbenzoic acid.
This reaction can be carried out by using Grignard reagents or similar methods.
Cyclization to Form Anthraquinone :
The key step in forming anthraquinone is cyclization.
Heat the benzoylbenzoic acid in the presence of dehydrating agents like concentrated sulfuric acid or other catalysts to promote the formation of the anthraquinone structure.
Oxidation to 9,10-Anthraquinone :
Finally, oxidize the resulting hydroxyl-anthrone intermediate to form 9,10-anthraquinone.
This oxidation can be achieved using strong oxidizing agents such as chromic acid or potassium dichromate.
Each of these steps involves careful control of reaction conditions, such as temperature, pressure, and choice of solvents, to ensure high yield and purity of the desired product. Anthraquinone has applications in dyes, pigments, and as a precursor for other complex organic compounds.
To synthesize 9,10-anthraquinone from benzene, begin with Friedel-Crafts acylation to form benzophenone, then conduct a carboxylation to create benzoylbenzoic acid. Cyclize this acid under acidic conditions to form the anthraquinone structure, and finally, oxidize the intermediate to obtain 9,10-anthraquinone. Each step requires careful control of conditions to ensure high yield and purity.
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