C1(C)C=CC(S[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)([CH3:11])[C:9]#[N:10])=CC=1.O.CCOCC>C(O)(=O)C.[Zn].S([O-])([O-])(=O)=O.[Cu+2]>[O:18]([C:14]1[CH:13]=[C:12]([CH:8]([CH3:11])[C:9]#[N:10])[CH:17]=[CH:16][CH:15]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1417 mg of alpha-(p-tolylthio)-alpha-(m-phenoxyphenyl)propionitrile was dissolved in 4 ml of acetic acid. Zinc powder (370 mg) and 25 mg of anhydrous copper sulfate were added. The mixture was heated under reflux for 1 hour with stirring. After the cooling, 20 ml of water and 20 ml of ether were added. The insoluble matter was separated by filtration. Sodium carbonate (5 g) was added to the filtrate to neutralize the acetic acid, followed by extraction with ether (15 ml×4 times). The extract was washed with 30 ml of water three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The oily residue was purified by column chromatography (silica gel; hexane and methylene chloride) to afford 247 mg (yield 92%) of alpha-(m-phenoxyphenyl)propionitrile as an oil. A sample for elemental analysis was prepared by subjecting the oil to bulb-to-bulb distillation [149°-154° C. (bath temperature)/1 torr].
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