Phenyl ether 3-Phenylethyl chloride

To the stirred solution of 5 parts of N-(4-piperidyl)propionanilide, 6.85 parts sodium carbonate, 0.05 part potassium iodide in 120 parts hexone is added portionwise a solution of 3.8 parts /3-phenylethyl chloride in 24 parts 4-methyl-2-penlanone. The mixture is stirred and refluxed for 27 hours. The reaction mixture is filtered while hot, and the filtrate is evaporated. The oily residue is dissolved in 160 parts diisopropyl ether and the solution is filtered several times until clear, then concentrated to a volume of about 70 parts. The residue is then cooled for about 2 hours at temperatures near 0°C to yield N-[1-((3-phenyl-ethyl)-4-piperidyl] propionanilide, melting at about 83° to 84°C as described in U.S. Patent 3,141,823. 

In a related series where non-concertedness was also apparent, the reaction of phenyl (l-phenylethyl)triazene with an excess of hydrogen chloride in ether yielded phenyl(1-phenylethyl) amine with 89% retention of configuration, as well as optically active ring-alkylated products and active 1-phenylethyl chloride No reasonable concerted process for forming these compounds comes to mind. Lastly, the isomerizations and skeletal rearrangements characteristic of the nitrosoamide de-... 

In the presence of dicarbonylrhodium chloride dimer [Rh(CO)2Cl]2, 1-benzoyl-2-propylcyclo-propene reacts with hex-l-yne to give 2-butyl-7-phenyl-4-propyloxepin (1, R = Pr) in 62% yield together with 2-butyl-6-phenyl-3-propylphenol. With methyl prop-2-ynyl ether and 4-phenyl-but-l-yne, 2-(methoxymethyl)-7-phenyl-4-propyloxepin (54%) and 7-phenyl-2-(2-phenylethyl)-4-propyloxepin (45%) are formed together with small amounts of the isomeric phenols.87... 

The cleavage of Te-C (phenyl) bonds was observed in reactions between diphenyl tellurium dichloride and 2-phenylethyl magnesium bromide in a diethyl ether/benzene medium at room temperature. Tris[2-phenylethyl telluronium bromide (m.p. 127°) and chloride (m.p. 135°) were isolated in approximately 40% yield4. 

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