Nitric Acid → 4-tert-Butyl-2-methyl-6-nitro-phenol

HRID 598719Notes

Reaction equation

HRID 598719 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 73794-Tert-Butyl-2-Methylphenol

Product 1

HCID 574185474-tert-Butyl-2-methyl-6-nitro-phenolYield 96.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-tert-Butyl-2-methyl-phenol (1.64 g, 10 mmol) was dissolved in 15 mL acetic acid, fuming nitric acid (0.47 mL, 10 mmol) was added and the resulting solution was stirred at rt overnight. The reaction mixture was then poured onto crushed ice, and extracted with chloroform. The organic phase was washed with water, and dried over sodium sulfate. Evaporation gave 2.02 g the nitration product as a red oil.

Workup

  1. additionThe reaction mixture was then poured
  2. customonto crushed ice
  3. extractionextracted with chloroform
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation

Sources & evidence

ORD record
ord-3466fad70d9e4cf2a60ec95cecf9a0d2
Source dataset
uspto-grants-2011_03
Patent number
US07897599B2

Reaction notes

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