2-(4-(benzyloxy)-2-methylphenyl)-N,N-dimethylacetamide → 2-(4-hydroxy-2-methylphenyl)-N,N-dimethylacetamide

HRID 1850724Notes

Reaction equation

HRID 1850724 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[C:11]([CH3:21])[CH:10]=1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]([CH3:19])[CH3:20])=[O:17])=[C:11]([CH3:21])[CH:10]=1

Participants

4

Reactant 1

HCID 708189752-(4-(benzyloxy)-2-methylphenyl)-N,N-dimethylacetamide

Product 1

HCID 867111812-(4-hydroxy-2-methylphenyl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

2-[4-(benzyloxy)-2-methylphenyl]-N,N-dimethylacetamide (680 mg, 2.40 mmol) was dissolved in ethanol (4 ml). and palladium hydroxide on carbon (20%) (169 mg, 0.240 mmol) added. The mixture was stirred under an atmosphere of hydrogen gas at RT overnight. The mixture was filtered and the filtrate concentrated under reduced pressure to afford the title compound. LC/MS (m/z): 194 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7ceebfc211ed427399250b59d1f9e844
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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