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

HRID 1988348Notes

Reaction equation

HRID 1988348 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17].C(O)(=O)C>C1CCCCC1>[C:11]([C:7]1[CH:8]=[C:9]([N+:16]([O-:18])=[O:17])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 314052,6-Di-tert-butylphenolHCID 86584207Acetic acid nitric acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

2,6-di-t-butylphenol (8 g, 39 mmoles) is dissolved in 25 ml of cyclohexane at 10° C. A (1/1) mixture of nitric acid/acetic acid (5 ml) is added dropwise to the reaction medium maintained at this temperature. Agitation is then carried out for 15 minutes at ambient temperature. Then the precipitate formed is filtered off, rinsed with water and pentane. The 2,6-di-t-butyl-4-nitrophenol obtained (6.34 g, 65%) is dried in an oven and will be used without further purification in the following stages. Pale yellow powder. Melting point: 167-168° C.

Workup

  1. additionis added dropwise to the reaction
  2. temperaturemedium maintained at this temperature
  3. customThen the precipitate formed
  4. filtrationis filtered off
  5. washrinsed with water and pentane

Sources & evidence

ORD record
ord-ed9a7c11ef4142f89721cc9229cfdeaf
Source dataset
uspto-grants-2009_06
Patent number
US07553976B2

Reaction notes

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