- Products of oxidative coupllng of phenol by horseradish peroxidase
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The oxidation and coupling of phenol by horseradish peroxidase in the presence of hydrogen peroxide yielded dimers trimers and higher molecular weight polymers which are mostly insoluble in water, so the products may be removed by centrifugation. However we discovered some products, such as dimers o,o'-biphenol, p,p'-biphenol, o,p'-biphenol, o-phenoxyphenol and p-phenoxyphenol, even though trimer 4-(4-phenoxyphenoxy)phenol were present in the aqueous phase at a very low concentration.
- Huixian,Taylor
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- A convenient method for the preparation of 4-aryloxyphenols
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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-aryl-oxybenzaldehydes, 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.
- Yeager,Schissel
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