O-Cresol → 2-Methyl-6-nitrophenol

HRID 234098

Reaction equation

HRID 234098 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[N+:9]([O-])([OH:11])=[O:10]>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:8]

Participants

4

Reactant 2

HCID 335O-CresolHCID 944Nitric Acid

Product 1

HCID 831032-Methyl-6-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To an ice-cooled solution of 2-methylphenol (10.8 g, 0.1-mmol) in acetic acid, fuming nitric acid (6.3 g) was slowly added with stirring to start reaction. The reaction mixture was stirred at a temperature of 20° C. or below for 1 h and thereafter poured into ice water. The reaction product was extracted with ethyl acetate and the extracted layer was washed with water, saturated sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride in the order written. Thereafter, the washed layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography with a benzene-ethyl acetate mixture used as eluant, thereby giving the desired compound, 2-methyl-6-nitrophenol, in an amount of 1.3 g.

Workup

  1. additionwas slowly added
  2. customreaction
  3. stirringThe reaction mixture was stirred at a temperature of 20° C. or below for 1 h
  4. extractionThe reaction product was extracted with ethyl acetate
  5. washthe extracted layer was washed with water, saturated sodium hydrogencarbonate
  6. dry with materialThereafter, the washed layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography with a benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-68ca6f3315114b1ba60a66fe1882727b
Source dataset
uspto-grants-1997_01
Patent number
US05594112

Linked notes

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