Naturally occurring phenolic compounds, especially those containing a meta-phenyldiol functional group, demonstrate significant antioxidant properties. Examples include resveratrol, catechin, quercetin, and chrysin to name a few. Hypochlorous acid (HOCl), is produced biologically by activated neutrophils, and, when produced in excess, can damage important biomolecules resulting in inflammation. The simplest meta-phenyldiol is resorcinol. Heasley, et al. (Env. Tox. & Chem, 1989) report that reactions involving a 1:1 mole ratio of resorcinol and HOCl result in significant amounts of multi-chlorinated resorcinol products. To explain this observation it is hypothesized that the dieneone intermediate produced during electrophilic aromatic substitution reacts faster with HOCl than it does with water even in an aqueous environment. Attempts to isolate the intermediate have been undertaken so that its chemical behavior can be examined experimentally. The experimental methodology used and the results of these experiments are the subject of this presentation.

Preparation and isolation of a reactive intermediate produced during electrophilic aromatic substitution of dichlororesorcinol

251st National Meeting (2016)

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