AQUEOUS HIGH-TEMPERATURE CHEMISTRY OF CARBOCYCLES AND HETEROCYCLES .9. AQUATHERMOLYSIS OF ORTHO-SUBSTITUTED, META-SUBSTITUTED, AND MULTISUBSTITUTED PHENOLS IN THE PRESENCE AND ABSENCE OF SODIUM BISULFITE

Aquathermolyses, with or without the addition of the Bucherer reagents, were studied for o- and m-cresol and 2-ethyl-, 2-isopropyl-, 2,4,6-trimethyl-, and 3,4,5-trimethylphenols. Ortho and para, but not meta, alkyl groups in the phenols are attacked readily by NaHSO3 with loss or conversion to lower alkyl groups, o-Ethyl- and isopropylphenols are converted after short reaction times into benzofurans, but on longer heating, the furan rings are reopened to give degradation of, or complete loss of, the original o-alkyl groups. © 1990, American Chemical Society. All rights reserved.