Nitric Acid → 2-Ethyl-6-nitrophenol

HRID 1723001Notes

Reaction equation

HRID 1723001 reaction equation
CCOCC.[CH2:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[CH3:7].[N+:15]([O-])([OH:17])=[O:16]>O>[CH2:6]([C:8]1[C:9]([OH:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][CH:13]=1)[CH3:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 69972-Ethylphenol

Product 1

HCID 150363132-Ethyl-6-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 130 ml of ether, 130 ml of water and 10.0 g of 2-ethylphenol was added dropwise 6.7 ml of 61% nitric acid, and the reaction was continued with stirring at room temperature for 4 hours. The reaction mixture was extracted with 300 ml of ethyl acetate and washed with a brine, and then 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 5.75 g of 6-ethyl-2-nitrophenol.

Workup

  1. extractionThe reaction mixture was extracted with 300 ml of ethyl acetate
  2. washwashed with a brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-c9bd3d9f9baa4e92a762890ff4b9b9ea
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Reaction notes

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