2-Methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol → 1-(4-Amino-2-methylphenoxy)-2-methylpropan-2-ol

HRID 906238Notes

Reaction equation

HRID 906238 reaction equation
[CH3:1][C:2]([OH:16])([CH3:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[CH3:14]>CO.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][C:2]([CH3:15])([OH:16])[CH3:1])=[C:6]([CH3:14])[CH:7]=1

Participants

4

Reactant 1

HCID 575406062-Methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol

Product 1

HCID 575405781-(4-Amino-2-methylphenoxy)-2-methylpropan-2-olYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol (7.30 g, 32.4 mmol) and 10% Pd/C (0.345 g, 3.24 mmol) in MeOH (150 mL) was hydrogenated at 1 atm of H2 for 18 hours. After removal of the Pd/C by filtration, the solution was concentrated to yield 1-(4-amino-2-methylphenoxy)-2-methylpropan-2-ol (6.10 g, 29.7 mmol, 92% yield) as clear gum which was carried forward without further purification.

Workup

  1. customAfter removal of the Pd/C
  2. filtrationby filtration
  3. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-832b8cffb34f457e80ee5912d21fe407
Source dataset
uspto-grants-2011_09
Patent number
US08012984B2

Reaction notes

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