Reactions of Allyl Phenyl Ether in High-Temperature Water with Conventional and Microwave Heating

Laurence Bagnell, Teresa Cablewski, Christopher R. Strauss,* and Robert W. Trainor
CSIRO Division of Chemicals and Polymers, Private Bag 10, Rosebank MDC, Clayton, Victoria 3169, Australia
J. Org. Chem., 1996, 61 (21), pp 7355–7359
DOI: 10.1021/jo961095j
Publication Date (Web): October 18, 1996
Copyright © 1996 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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In a systematic study, allyl phenyl ether (1) was heated in water for 1 h at temperatures of 180 °C and above. Parallel experiments were conducted with a conventionally heated autoclave and a recently developed microwave batch reactor. Relatively modest temperature differences resulted in diverse product distributions, and these were independent of the method of heating. Maximum conversion of 1 to 2-allylphenol occurred at 200 °C (56%) and to 2-methyl-2,3-dihydrobenzofuran at 250 °C (72%). Although 2-(2-hydroxyprop-1-yl)phenol comprised less than 1% of the product mixture at both 180 and 260 °C, it accounted for 37% at 230 °C. The reaction sequence was investigated by heating intermediates individually at selected temperatures up to 290 °C. Hydration of 2-allylphenol to 2-(2-hydroxyprop-1-yl)phenol was partially reversible. The work showed that high-temperature water constitutes an environmentally benign alternative to the use of acid catalysts or organic solvents and offers scope for interconversion of alcohols and alkenes.

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History

  • Published In Issue October 18, 1996
  • Received June 11, 1996

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