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

HRID 2373760Notes

Reaction equation

HRID 2373760 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-803761993aa04e9abfbc962c47714e05
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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