2,4-Dichloro-3-methyl-6-nitrophenol

Description

2,4-Dichloro-3-methyl-6-nitrophenol is a hydrocarbon solvent that is used in the synthesis of nitrotoluene. It is also used as an intermediate in the production of chlorinated phenols. The chlorination can be achieved by reacting 2,4-dichloro-3-methylphenol with hydrochloric acid and chlorine gas. The reaction with hydrochloric acid produces 2,4,6-trichlorophenol and 2,4-dichlorophenol. The reaction with chlorine gas produces 2,4,5-, and 3,5-, trichlorophenols. This chemical has been widely used in the production of organic solvents such as carbon tetrachloride and nitrobenzene.

Synthesis

2,4-Dichloro-3-methyl-6-nitrophenol 2 was prepared by KOH/H2O hydrolysis of a product mixture obtained from chlorination of p-nitrotoluene in the presence of a phase transfer catalyst. A 95–99% yield of 2 based on 2,3,6-trichloro-4-nitrotoluene, 4 (major chlorination product) was achieved in >95% purity^[1].

References

[1] R. RAN  C. P. A Practical Synthesis of 2,4-Dichloro-3-methyl-6-nitrophenol[J]. Synthetic Communications, 1993. DOI:10.1080/00397919308013809.