Some phenols, particularly those activated by nitro-, carboxyl, or other meta-directing groups in the ortho or para positions are known to react with phosphorus pentachloride with replacement of the phenolic hydroxyl by chlorine. This transformation has also been accomplished in some cases by treating the phenol with p-toluenesulfonyl chloride in the presence of a tertiary amine such as N,N-dimethylaniline. A notable example of the latter reaction is the conversion of 2,4-dinitro-naphthol to 2,4-dinitro-1-chloronaphthalene (1). We have studied the replacement of phenolic hydroxyl by chlorine in several different cases. Our results suggest that the nature of the reaction may be influenced both by the activating effect of the other ring substituents and also by the steric effects of the other substituents.
Proceedings of the Iowa Academy of Science
©1953 Iowa Academy of Science, Inc.
Smith, Walter T. Jr. and Campanaro, Louis
"The Replacement of Aromatic Hydroxyl by Chlorine,"
Proceedings of the Iowa Academy of Science, 60(1), 319-324.
Available at: https://scholarworks.uni.edu/pias/vol60/iss1/40