Nitric Acid → 3,6-Dimethyl-2-nitrophenol

HRID 1723011Notes

Reaction equation

HRID 1723011 reaction equation
CCOCC.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[OH:14].[N+:15]([O-])([OH:17])=[O:16]>O>[CH3:13][C:10]1[C:9]([N+:15]([O-:17])=[O:16])=[C:8]([OH:14])[C:7]([CH3:6])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 72672,5-Dimethylphenol

Product 1

HCID 2596513,6-Dimethyl-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 130 ml of water, 130 ml of ether and 10.0 g of 2,5-dimethylphenol was added dropwise 5.2 ml of 70% nitric acid while cooling with ice. The temperature of the mixture was raised to room temperature and the reaction was continued for a day. After 500 ml of water was added, the reaction mixture was extracted with 500 ml of ethyl acetate, washed with water and a brine successively, and dried with anhydrous sodium sulfate. The drying agent was filtered off and the solvent was distilled away under reduced pressure. The residue was purified by subjecting to silica-gel column-chromatography [eluent:chloroform] to give 3.83 g of 3,6-dimethyl-2-nitrophenol.

Workup

  1. temperaturewhile cooling with ice
  2. waitthe reaction was continued for a day
  3. extractionthe reaction mixture was extracted with 500 ml of ethyl acetate
  4. washwashed with water
  5. dry with materiala brine successively, and dried with anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe residue was purified

Sources & evidence

ORD record
ord-10d6bb0c26114a3c90fb31cbe2bdff73
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Reaction notes

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