2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile → 2-(5-(tert-Butyl)-2-hydroxyphenyl)-2-methylpropanenitrile

HRID 2401658Notes

Reaction equation

HRID 2401658 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.[OH-].[OH-].[Pd+2]>[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

4

Reactant 1

HCID 595441512-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile

Product 1

HCID 595441652-(5-(tert-Butyl)-2-hydroxyphenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

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

  1. filtrationThe mixture was then filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5538d8299f394abd89dcb317c7eba5d7
Source dataset
uspto-grants-2014_08
Patent number
US08796308B2

Reaction notes

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