81455-06-3

Basic information

• Product Name: trans-1-Phenyl-2-phenoxycyclohexan-1-ol
• CAS NO: 81455-06-3
• Molecular Weight: 268.356
• Mol File: 81455-06-3.mol

Chemical Properties

• CAS DataBase Reference: trans-1-Phenyl-2-phenoxycyclohexan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: trans-1-Phenyl-2-phenoxycyclohexan-1-ol(81455-06-3)
• EPA Substance Registry System: trans-1-Phenyl-2-phenoxycyclohexan-1-ol(81455-06-3)

Safety Data

• Hazardous Substances Data: 81455-06-3(Hazardous Substances Data)

Upstream product

• 27167-34-6 trans-1-Phenylcyclohexane-1,2-diol 
• 28899-97-0 triphenylbismuth(V) diacetate 

Relevant articles and documents

SELECTIVE PHENYLATION IN MILD CONDITIONS OF ONE HYDROXY GROUP IN GLYCOLS WITH TRIPHENYLBISMUTH DIACETATE: A NEW SPECIFIC GLYCOL REACTION.

Refluxing for 4-5 h a dichloromethane solution of diol in the presence of an equimolecular quantity of triphenylbismuth diacetate gave the monophenyl ether in good to excellent yield.

Conversion of One Hydroxy Group in a Diol to a Phenyl Ether with Triphenylbismuth Diacetate, a New Glycol Reaction Showing Strong Axial Preference in Six-Membered Rings

After being refluxed for a few hours, a dichloromethane solution of a diol with triphenylbismuth diacetate gave in most cases excellent yields of a monophenyl ether.No diphenylated products were found.Tertiary hydroxy groups were only phenylated in bis tertiary diols, and then in poor yield.Increasing the distance between the hydroxy groups up to six carbon atoms decreased the speed of the reaction which nevertheless was still preparatively useful.Diols in flexible rings behaved like their acyclic counterparts.The course of the reaction was also examined with someconformationally rigid molecules: trans-4-tert-butyl-cis-2-hydroxycyclohexanol, trans-4-tert-butyl-trans-2-hydroxycyclohexanol, cholestane-2α,3α-diol, cholestane-2α,3β-diol, and pyranoside derivatives with the α-D-gluco, α-D-manno, α-D-galacto, and α-D-allo configurations.The phenylations of cis-diols were strongly regioselective for axial epimers, while those of trans, bis equatorial diols were undiscriminate and often much slower.A feasible general mechanism is proposed to explain these results.