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

HRID 2353551Notes

Reaction equation

HRID 2353551 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-a909488f2b9e4f4b843aa57a213f567b
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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