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

HRID 1988333Notes

Reaction equation

HRID 1988333 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]([OH:14])=[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=1)([O-])=O.[H][H]>C(O)C.ClCCl.[Pd].CCCCCCC>[NH2:1][C:4]1[CH:5]=[C:6]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:7]([OH:14])=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1

Participants

7

Reactant 2

HCID 697652,6-Di-tert-butyl-4-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 3142204-Amino-2,6-di-tert-butylphenolYield 50%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8900HeptaneSolventHCID 23938PalladiumSolvent

Procedure

In a 250 ml Parr flask, 3.6 g (14 mmoles) of 4-nitro-2,6-bis-(1,1-dimethylethyl)-phenol (J. Org; Chem. (1968), 33 (1), 223-226) is dissolved in 60 ml of a (2/1) mixture of ethanol and dichloromethane in the presence of a catalytic quantity of 10% Pd/C. The mixture is agitated for 2 hours, at 20° C., under 20 PSI of hydrogen. After filtration on celite, the filtrate is concentrated to dryness under reduced pressure. The reddish-brown powder obtained is suspended in heptane (30 ml), filtered and rinsed with the same volume of heptane. The expected product is obtained in the form of an salmon pink powder with a yield of 50% (1.56 g). Melting point: 123-124° C.

Workup

  1. filtrationAfter filtration on celite
  2. concentrationthe filtrate is concentrated to dryness under reduced pressure
  3. customThe reddish-brown powder obtained
  4. filtrationfiltered
  5. washrinsed with the same volume of heptane

Sources & evidence

ORD record
ord-ff1951bcab0f493fad90075b7845102d
Source dataset
uspto-grants-2009_06
Patent number
US07553976B2

Reaction notes

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