2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile → 2-(5-(tert-Butyl)-2-hydroxyphenyl)-2-methylpropanenitrile
Reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][C:10]=1[C:19]([CH3:23])([CH3:22])[C:20]#[N:21])C1C=CC=CC=1>CO>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([C:19]([CH3:23])([CH3:22])[C:20]#[N:21])[CH:11]=1)([CH3:18])([CH3:16])[CH3:17]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Pd (OH)2/C (2.0 g) and compound 7 (20.0 g, 0.104 mol) were stirred in MeOH (150 mL) at room temperature under hydrogen at 10 psi pressure for 16-18 hours. The mixture was then filtered through a pad of Celite®, and the filtrate was concentrated to give compound 15, which was used in the next reaction without further purification. 1H NMR (DMSO-d6; 400 MHz) δ 9.83 (s), δ 7.24 (s), δ 7.18 (m), δ 6.80 (m), δ 1.71 (s), δ 1.24 (s).
Workup
- filtration