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A procedure is described for the identification of phenolic compounds by paper chromatography. 2. Examples are given of the use of the method in metabolic studies. 3. All the theoretically possible oandp-hydroxylation products have now been identified in rabbit urine after administration of the o-, m-and phydroxybenzoic acids and amides. 4. It has been shown that both salicylic acid and m-hydroxybenzoic acid are conjugated with glycine in the rabbit. The authors thanks are due to Dr R. Consden for his advice in preliminary discussions on the technique of paper chromatography. We are indebted to the Royal Society for a Government Grant which defrayed part of the cost of this work. Some micro-analyses were carried out by Drs Weiler and Strauss, Oxford.

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In the rabbit 2:3:5:6-tetrachloronitrobenzene is metabolized by reduction of the nitro group, hydroxylation and mercapturic acid formation (Bray, Hybs, James & Thorpe, 1953). The last reaction is of particular interest since it is accompanied by loss of a nitro group directly attached to the benzene ring. Two further examples of this type of reaction were encountered when pentachloronitrobenzene and 2:3:4:6-tetrachloronitrobenzene were given to rabbits (Betts, James & Thorpe, 1953). A more detailed study of the metabolism of these two compounds is now reported. The stability of the nitro group in pentachloro-, the tetrachloro-and three trichloro-nitrobenzenes has been examined in relation to formation of mercapturic acids from the highly chlorinated nitrobenzenes. METHODS Melting points are uncorrected. Materials. Pentachloronitrobenzene, m.p. 1460, was supplied by Bayer Agriculture Ltd. and Hickson and Welch Ltd. and 2:3:5:6-tetrachloronitrobenzene, m.p. 990, by Bayer Agriculture Ltd. 2:3:4:6-Tetrachloronitrobenzene, m.p. 410, was prepared from 2:4:6-trichloroaniline, which was converted by a Sandmeyer reaction into 1:2:3:5tetrachlorobenzene; this was nitrated by refluxing for 0-5 hr. with HNO3 (sp.gr. 1-52) to give 2:3:4:6-tetrachloronitrobenzene. (Details were kindly supplied by Dr M.