3-(4-Aminophenyl)-1-(4-methylphenyl)propan-1-one → 3-(4-aminophenyl)-1-(4-methylphenyl)propan-1-ol

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[H][H]>O1CCCC1.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:18])[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

Procedure

60 g of the 1-(4-methylphenyl)-3-(4-aminophenyl)-n-propan-1-one prepared as described in Example A were hydrogenated, in 1 liter of tetrahydrofuran, in the presence of 5 g of 10% strength Pd on charcoal, under 1.1 bar, until 5.5 liters of hydrogen had been absorbed. The catalyst was separated off and the reaction solution was evaporated down, and the oil obtained crystallized on trituration with diisopropyl ether. After the white crystals had been dried, 53 g (88% of theory) of the carbinol of melting point 63°-65° C. were obtained.