Article

Synthesis of Substituted Resorcinol Monomethyl Ethers from 2-Bromo-3-methoxycyclohex-2-en-1-ones

Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada
J. Org. Chem., 2015, 80 (6), pp 3211–3216
DOI: 10.1021/acs.joc.5b00192
Publication Date (Web): February 19, 2015
Copyright © 2015 American Chemical Society

Abstract

Abstract Image

2-Bromo-3-methoxycyclohex-2-en-1-ones are readily alkylated at C-6 with reactive halides, and then treatment with DBU (2 equiv) in PhMe at room temperature results in smooth loss of bromide and aromatization to resorcinol monomethyl ethers of defined substitution pattern.

Supporting Information


Copies of NMR spectra of 1, 2, 4, 1426, 28, 30, 31, 33, and 34 and an ORTEP diagram and X-ray data (CIF) for compound trans-2. This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 887 Times
Received 27 January 2015
Published online 19 February 2015
Published in print 20 March 2015
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