2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropan-1-ol → 4-(tert-Butyl)-2-(1-hydroxy-2-methylpropan-2-yl)phenol

HRID 1617293Notes

Reaction equation

HRID 1617293 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])[CH2:20][OH:21])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:16])[CH3:17])=[CH:11][C:10]=1[C:19]([CH3:23])([CH3:22])[CH2:20][OH:21]

Participants

4

Reactant 1

HCID 595441642-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropan-1-ol

Product 1

HCID 595441604-(tert-Butyl)-2-(1-hydroxy-2-methylpropan-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Pd(OH)2 (1 g) and compound 9 (9.26 g, 0.030 mol) in MeOH (200 mL) were stirred under hydrogen at 20-30 psi pressure for 16-18 hours. The mixture was then filtered through Celite®, and the filtrate was concentrated to give compound 10 as a white solid. 1H NMR (DMSO-d6; 400 MHz) δ 9.16 (s), δ 7.16 (d), δ 7.00 (m), δ 6.65 (m), δ 4.71 (t), δ 3.62 (d), δ 1.27 (s), δ 1.22 (s).

Workup

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

Sources & evidence

ORD record
ord-428102bf5d814a3ca7d9548895950a4b
Source dataset
uspto-grants-2014_07
Patent number
US08765957B2

Reaction notes

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