[CH3:1][CH:2](O)[CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1.[NH3:14].[H][H]>[Cr].[Cu]>[CH3:12][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([CH3:11])[CH:8]=1)[O:4][CH2:3][CH:2]([NH2:14])[CH3:1]A 150 cc autoclave was charged with 30.0 g (166 mmol) of 1-methyl-2-(3,5-dimethylphenoxy)ethanol, 3.0 g of a copper-chromium catalyst (N203SD, supplied by Nikki Chemical Co., Ltd.: CuO 44%, Cr2O3 44%, MnO2 5G %) and 30.0 g of a solvent (toluene). Further, 9.6 g (564 mmol) of ammonia was added, a hydrogen pressure of 40 kg/cm2G was applied, and then the temperature of the mixture was increased up to 240° C. The mixture was stirred at a reaction pressure of 104 to 97 kg/cm2G for 7 hours. The reaction mixture was allowed to cool, and the pressure of an excess of ammonia and hydrogen was released. Then, the catalyst was removed by filtration. The resultant filtrate was extracted with 100 ml of a 20% hydrochloric acid aqueous solution. The extracted aqueous layer was neutralized with a 20% sodium hydroxide aqueous solution, and 200 ml of ethyl ether was added to the aqueous layer for extraction. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to give 15.2 g of the intended compound, 1-(3,5-dimethylphenoxy)-2-aminopropane (yield 51%). The selectivity to the intended compound, calculated on the basis of the total amount of the starting compound, was 81%.
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