[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:20]=[CH:19][C:11]([O:12][CH:13]([CH3:18])[C:14]([NH:16][CH3:17])=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O>[F:1][C:2]([F:23])([F:24])[C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:20]=[CH:19][C:11]([O:12][CH:13]([CH3:18])[CH2:14][NH:16][CH3:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1In this example, 13.3 g (0.0392 mole) of α-[4-(4-trifluoromethylphenoxy)-phenoxy]-N-methylpropionamide was added portionwise to a stirred slurry containing 1.5 g (0.0392 mole) of lithium aluminum hydride. The resulting mixture was refluxed for 18 hours and then chilled to about 0° C. Then 1.6 ml of water, 1.6 ml of aqueous 15% by weight sodium hydroxide, and 4.8 ml of water were successively added to the chilled mixture and the resulting mixture was stirred until a white precipitate formed. Magnesium sulfate was then added to the mixture to absorb water and then the mixture was filtered. The filter cake was washed thoroughly with ethyl ether. The combined filtrate and ethyl ether washings was evaporated under vacuum affording an oil which crystallized upon standing. Infrared spectrographic examination showed incomplete reduction and accordingly the solid was dissolved in 300 ml of ethyl ether and then 1.5 g of lithium aluminum hydride was added portionwise to this solution. The resulting mixture was refluxed for 18 hours and then chilled to about 0° C. while water (1.5 ml), aqueous (15% by weight), sodium hydroxide (1.5 ml) and water (4.5 ml) were successively added. The mixture was then stirred until a white precipitate separated out. Magnesium sulfate was added and the mixture then filtered and the filter cake washed with methylene chloride. The combined filtrate and washing was evaporated under vacuum affording the title compound as an oil. Complete reduction was confirmed by infrared spectrography and n.m.r. analysis.
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