2-Chlorobenzoic acid is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula ClC₆H₄CO₂H. It is one of three isomeric chlorobenzoic acids, the one that is the strongest acid. This white solid is used as a precursor to a variety of drugs, food additives, and dyes.Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. .

Synthesis and reactions

It is prepared by the

oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...

of 2- chlorotoluene. The laboratory scale reaction employs

potassium permanganate Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, that dissolves in water as K+ and , an intensely pink to purple solution. Potassium permanganate is widely used in the c ...

. Alternatively it arises by the hydrolysis of α,α,α-trichloro-2-toluene. The chloride is readily replaced by ammonia to

2-aminobenzoic acid Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ''ortho''-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic f ...

. Similarly, the chloride is displaced by diphenylphosphide, leading to

2-diphenylphosphinobenzoic acid 2-Diphenylphosphinobenzoic acid is an organophosphorus compound with the formula (C6H5)2PC6H4CO2H. It is a white solid that dissolves in polar organic solvents. The ligand is a component of catalysts used for the Shell higher olefin process. It ...

. At elevated temperature it decarboxylates.

References

Benzoic acids Chlorobenzenes {{organohalide-stub