406700-77-4

Basic information

• Product Name: Phenol, 4-phenoxy-, formate
• CAS NO: 406700-77-4
• Molecular Formula: C13H10O3
• Molecular Weight: 214.221
• Mol File: 406700-77-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Phenol, 4-phenoxy-, formate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 4-phenoxy-, formate(406700-77-4)
• EPA Substance Registry System: Phenol, 4-phenoxy-, formate(406700-77-4)

Safety Data

• Hazardous Substances Data: 406700-77-4(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 459-57-4 4-fluorobenzaldehyde 
• 67-36-7 4-phenoxy benzaldehyde 
• 26944-31-0 N,N-Diformylacetamide 
• 831-82-3 4-Phenoxyphenol 

Downstream Products

• 133387-14-1 4-(4'-phenoxyphenoxy)acetophenone 
• 83246-64-4 4-(4-phenoxyphenoxy)benzaldehyde 
• 10181-94-9 ((p-Phenoxy)-4-phenoxy)phenol 
• 831-82-3 4-Phenoxyphenol 

Relevant articles and documents

One-pot synthesis of phenols from aromatic aldehydes by Baeyer-Villiger oxidation with H2O2 using water-tolerant Lewis acids in molecular sieves

The heterogeneous oxidation systems Sn-Beta/H2O2 and Al-Beta/H2O2 were both active for the Baeyer-Villiger oxidation of aromatic aldehydes. With alkoxy substituents in ortho and especially in para position, the corresponding formate ester was the primary reaction product with excellent selectivity. The highest selectivity toward the ester was obtained with the Sn-Beta catalyst in dioxane as solvent. High selectivities of the corresponding phenol could be obtained by employing ethanol or aqueous acetonitrile as solvent with Sn-Beta. Al-Beta was more efficient as catalyst for both Baeyer-Villiger oxidation and ester hydrolysis and, thus achieved high yields for the corresponding alcohol. However, this was a less selective catalyst than Sn-Beta zeolite. Sn-Beta was a chemoselective catalyst when the aldehyde reactant contained olefinic groups in an alkyl chain. With these reactants, the Al-zeolite gave no activity. Other classical BV oxidants, e.g., peracids, also yielded the epoxidation products. Thus, Sn-Beta catalysts open a new entry to aromatic phenols with unsaturated alkyl substituents that are interesting intermediates in the chemical industry.

A convenient method for the preparation of 4-aryloxyphenols

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.