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Synthesis 1991; 1991(1): 63-68
DOI: 10.1055/s-1991-26381
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A Convenient Method for the Preparation of 4-Aryloxyphenols

Gary W. Yeager* , David N. Schissel
  • *Polymer Chemistry Laboratory, General Electric Research and Development Center, P.O. Box 8, Schenectady, NY 12301, USA
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Publication Date:
17 September 2002 (online)

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A convenient method for the preparation of 4-aryloxyphenols via the homologation of preformed phenols is described. Condensation of various 4-substituted phenols with either 4-fluorobenzaldehyde (8) or 4-fluoroacetophenone (9) yielded the corresponding 4-aryloxybenzaldehydes, 10, and acetophenones, 11, in 70-93 % yield. Baeyer-Villiger oxidation of these materials with 3-chloroperoxybenzoic acid (MCPBA) yielded the corresponding 4-formyloxy and 4-acetoxyphenyl ethers which were hydrolyzed without purification to the desired 4-aryloxyphenols 12 in 72-94 % yield. Both 4-fluorobenzaldehyde (8) and 4-fluoroacetophenone (9) are synthetically equivalent to the a4 umpoled synthon 6. Extension of this methodology of the preparation of 4,4′-[arylbis(oxy)]bisphenols from aromatic diols is also described. Condensation of various aromatic diols with 8 or 9 yielded the corresponding 4,4′[arylbis(oxy)]bisbenzaldehydes 15 and acetophenones 16 in 71-89 % yield. Baeyer-Villiger oxidation of these compounds with MCPBA yielded the desired 4,4′-[arylbis(oxy)]bisphenyl bisformates 17 and bisacetates 18 in 67-84 % yield. Hydrolysis of these compounds afforded the desired 4,4′-[arylbis(oxy)]bisphenols 19 in 70-91% yield.

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