2-Chloro-''m''-cresol is a chlorinated

cresol Cresols (also known as hydroxytoluene, toluenol, benzol or cresylic acid) are a group of aromatic organic compounds. They are widely-occurring phenols (sometimes called ''phenolics'') which may be either natural or manufactured. They are also c ...

. The compound is difficult to synthesise as chlorination of ''m''-cresol yields the ''para''-product (4-chloro-3-methylphenol). Historically synthesis has been achieved via a para-selective

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...

, followed by conversion to a

diazonium compound Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, compou ...

and a

Sandmeyer reaction The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides ...

to insert the chlorine into the 2-position.

Related compounds

4-Chloro-3-methylphenol ''p''-Chlorocresol, or 4-chloro-3-methylphenol (ClC6H3CH3OH), also known as p-chloro-m-cresol, is a potent disinfectant and antiseptic. It appears as a pinkish white crystalline solid. It is also used as a preservative in cosmetics and medicina ...

(PCMC) - similar structure * 4-Chloro-3,5-dimethylphenol (PCMX) - similar structure

References

{{aromatic-stub Chlorobenzene derivatives Cresols