The Synthesis of 4-Tosyloxy-2-Substituted Phenols using New Solid Pyridinium Salt Supported [Hydroxyl(Tosyloxy)Iodo]Benzene Reagents

Author:

Yang Bing12,Zhang Jizhen1,Zhao Dejian1,Kuang Hua1

Affiliation:

1. School of Chemistry and Environmental Engineering, Jiangsu Teachers University of Technology, Changzhou, Jiangsu 213001, P. R. China

2. School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China

Abstract

Two new solid pyridinium salt supported HTIB reagents ( N-{4-[hydroxyl(tosyloxy)iodo]benzyl}pyridinium tetrafluoroborate and N-{4-[hydroxyl(tosyloxy)iodo]phenylcarbamoylmethyl}pyridinium tetrafluoroborate) were synthesised using a pyridinium salt as a cationic support. Although the former was hygroscopic the latter was stable in air and in a highly humid atmosphere over a few weeks. The latter has an extra amide linkage. The structures of both compounds were established by IR, 1H NMR, 13C NMR, MS and elemental analysis. Then, two 4-tosyloxy-2-substituted phenols were successfully prepared using the new reagents. Both reagents were easily regenerated in high yields.

Publisher

SAGE Publications

Subject

General Chemistry

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