P-Phenylethyl iodide

P-Phenylethyl alcohol, 812,816 Phenylethylene, 1015,1024 a-Phenylethylamine, 560, 566 P-Phenylethy,amine, 560, 567,569 Phenylethylbarbituric acid, 1003,1005 P-Phenylethyl bromide, 283 P-Phenylethyl iodide, 288 Phenylglycine-o-carboxylic acid, 980 Phenylglyoxal, 866 Phenylhydrazine, 635, 636 hydrochloride, 636, 637 Phenylhydrazine acetate reagent, 343, 721 ... 

Phenylethyl Iodide. Use 146 g. (142 ml.) of (J-phenylethyl alcohol (b.p. 216 5-217°), 16 54 g. of purified red phosphorus and 154 g. of iodine. Lag the arm C (Fig.///, 40, 1) with asbestos cloth. Heat the alcohol - phosphorus mixture to boiling until sufficient alcohol (usually one-third to one-half of the total volume) passes into the reservoir B to dissolve all the iodine. Remove the flame and add the iodine solution at such a rate that the mixture boils gently. A little hydrogen iodide is evolved towards the end of the reaction. Allow the mixture to cool, add water and filter off the excess of phosphorus. Decolourise the filtrate with a little sodium bisulphite and add ether to assist in the separation of the water layer. Wash the ethereal solution with water, dry with anhydrous potassium carbonate, and distil under diminished pressure. B.p. 114 116°/12 mm. Yield 215 g. 

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 p-phenylethyl chloride in 24 parts 4-methyl-2-pentanone. 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-[l-(P-phenylethyl)-4-piperidyl]propionanilide, melting at about 83° to 84°C as described in US Patent 3,141,823. 

We examined the polymerization of St at 80 °C, using 1-phenylethyl iodide (PE-I) as a low-mass alkyl halide initiator, GeLi as a deactivator, and benzoyl peroxide (BPO) as a conventional radical initiator. In this polymerization, P, which is originally supplied by BPO, is supposed to react with Gel4, in situ producing the activator Gelj (and P-I). If Gel effectively abstracts I from PE-I (or P-I) to produce PE (or P ), a useful sequence of activation and deactivation will be completed. 

Diethyl phenylphosphinite, C6H5.P(OC2H5)2, is formed when phenyldichlorophosplune reacts with sodium ethoxide it is a colourless, mobile liquid, B.pt. 235° C., density 1 032 at 16° C., insoluble in water in contact with ethyl iodide it isomerises to ethyl phenylethyl-phosphinate, (C2H5)(C6H5)PO.OC2Hs. 

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