[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[CH2:11][C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](Cl)[CH2:18][CH2:19][CH3:20].[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC)C.O>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]([CH2:17][CH2:18][CH2:19][CH3:20])[C:12]#[N:13])[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Into a three-necked 500 ml round-bottom flask are charged 35 g (0.17 mole) of m-phenoxybenzyl cyanide, 16.3 g (0.17 mole) of butyl chloride 4 g of tetraethylammonium bromide. To this mixture is added 27 g (0.34 mole) of 50% sodium hydroxide solution dropwise with stirring. The reaction mixture is heated at 90° for three hours. It is then poured into water and extracted with hexane. The combined hexane extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 39 g of crude product. Vacuum distillation (149°-155°/0.2 mm) provides 24.7 g of pure product.
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