2,6-Di-tert-butyl-4-nitrophenol → 4-Amino-2,6-di-tert-butylphenol

HRID 2086548Notes

Reaction equation

HRID 2086548 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=1[OH:18])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=1[OH:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 697652,6-Di-tert-butyl-4-nitrophenol

Product 1

HCID 3142204-Amino-2,6-di-tert-butylphenolYield 48.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,6-di-t-butyl-4-nitrophenol (6.3 g, 25 mmoles) is dissolved in methanol (100 ml). 0.6 g of palladium on carbon (10%) is added and the whole is placed under a hydrogen atmosphere under 2 bars of pressure. The catalyst is filtered out and the solvent is evaporated off under reduced pressure. The residue is taken up in heptane and filtered. In this way 2,6-di-t-butyl-4-aminophenol (2.7 g, 48%) is obtained which will be used without other purification in the following stages. Pink powder. Melting point: 123-124° C.

Workup

  1. filtrationThe catalyst is filtered out
  2. customthe solvent is evaporated off under reduced pressure
  3. filtrationfiltered

Sources & evidence

ORD record
ord-78fc376efeda4aa0a2fc25380292f609
Source dataset
uspto-grants-2004_04
Patent number
US06727239B1

Reaction notes

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