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Synthesis 1995; 1995(1): 28-30
DOI: 10.1055/s-1995-3859
short paper
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An Umpoled Synthon Approach to the Synthesis of 2-Aryloxyphenols

Gary W. Yeager* , David N. Schissel
  • *General Electric Research and Development Center, 1 River Road, Schenectady, New York, 12309, USA
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Publication Date:
31 December 2000 (online)

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A convenient three-step method for the preparation of 2-aryloxyphenols from phenols and 2-fluorobenzaldehyde is described. Condensation of phenols with 2-fluorobenzaldehyde produces the intermediate 2-aryloxybenzaldehydes in 83-95% yield. These products rapidly undergo meta-chloroperbenzoic acid (m-CPBA) promoted Baeyer-Villiger oxidation to yield the corresponding 2-aryloxyphenyl formates which are hydrolyzed, without isolation, to give the desired 2-aryloxyphenols in 79-96% yield.

umpoled synthon - 2-aryloxyphenols - aromatic nucleophilic displacement - Baeyer-Villiger rearrangement - Ullman ether synthesis - phenyl ether