Question

Propose a synthetic sequence of this trisubstituted benzene starting from toluene.

Short answer

Permanganate oxidation is a brutal oxidizing agent where OH and NH₂substituents do not survive.

Halogens (X), nitro (-NO₂), and SO₃H group survive the permanganate oxidation.

Step-by-step solution

Permanganate Oxidation

Permanganate oxidation is a brutal oxidizing agent where OH and NH₂substituents do not survive.

Halogens (X), nitro (-NO₂), and SO₃H group survive the permanganate oxidation.

Synthesis of tri-substituted benzene starting from toluene.

The substitution of the chlorine group with toluene is performed by chlorination in the presence of AlCl₃.

A carboxylic acid (COOH) group is attached to the benzene ring by oxidizing alkyl benzene. Here, the oxidation of the methyl group forms the carboxylic acid.

The product formed undergoes nitration. The nitration of the given group forms the final product.