C([O:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[C:8]([N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])=O)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CCOCC.O>[OH:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[CH2:8][N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14]
A mixture of 33.0 g (0.133 m) of 3-acetoxy-N,N-dibutylbenzamide in 400 ml of ether was slowly added over one half hour to a suspension of 5.0 (0.133 m) grams of lithium aluminum hydride (LAH) in 300 ml of ether. The mixture was heated to reflux for 2 hours. The mixture was slowly treated with 5.0 ml of water, 5.0 ml of 15% sodium hydroxide and 15.0 ml of water. Magnesium sulfate was added and stirred well. The mixture was filtered and washed well with ether. The solvent was evaporated off leaving the 3-hydroxy N,N-dibutylbenzylamine product in a yield of 23.3 g. The product was a yellow oil with a refractive index of n(25/D)=1.5172.
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