Synthesis of 2,6‐dimethoxy [U‐14C] phenol
- 1 January 1974
- journal article
- research article
- Published by Wiley in Journal of Labelled Compounds and Radiopharmaceuticals
- Vol. 10 (1) , 151-160
- https://doi.org/10.1002/jlcr.2590100117
Abstract
The preparation of 2, 6‐dimethoxy [U‐14C]phenol was carried out in five steps from [U‐14C]phenol. [U‐14C]Phenol was converted to 2‐[U‐14C]phenoxy‐5‐nitrobenzophenone which was sequentially hydroxylated with hydrogen peroxide‐acetic acid to give the di‐ortho hydroxylated phenolic intermediate, 2‐(2′',6″‐dihydroxy [U‐14C]phenoxy)‐5‐nitrobenzophenone. Methylation of this intermediate and subsequent scission of the aryl ether link with piperidine gave the required di‐ortho substituted phenol. An alternative sequence was investigated for the conversion of 2‐(2″‐hydroxy‐phenoxy)‐5‐nitrobenzophenone to 2‐(2″,6″‐dimethoxyphenoxy)‐5‐nitrobenzophenone but it gave a poorer overall yield with an unstable intermediate. Characterization data are included.Keywords
This publication has 2 references indexed in Scilit:
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- 55. ortho-Hydroxylation of phenols. Part III. Derivatives of pyrogallolJournal of the Chemical Society, 1953