Highly selective oxidative monochlorination to synthesize organic intermediates: 2-chlorotoluene, 2-chloroaniline, 2-chlorophenol, and 2-chloro-4-methylphenol

An alternative manufacturing process scheme was developed to synthesize mon ochloro-substituted aromatic compounds in high selectivity, involving oxida tive chlorination by using HCl-H2O2. Thus, 2-chlorotoluene, 2-chloroaniline , and 2-chlorophenol were synthesized by oxidative chlorination followed by desulphonation or decarboxylation, Oxidative chlorination of 4-methylbenze nesulphonic acid, 4-methylbenzoic acid, 4-aminobenzoic acid, and l-hydroxyb enzoic acid by using a suitable ratio of reactant:HCl:H2O2, and their subse quent desulphonation or decarboxylation, gave 60-85% yield of the desired p roducts. Oxidative chlorination of 4-methylphenol by using HCl-H2O2 gave as high as 98% selectivity to the desired 2-chloro-4-methylphenol.