Nitric Acid → 4-Cyclohexyl-2-nitrophenol

HRID 1723009Notes

Reaction equation

HRID 1723009 reaction equation
CCOCC.[CH:6]1([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[N+:19]([O-])([OH:21])=[O:20]>O>[CH:6]1([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 143274-Cyclohexylphenol

Product 1

HCID 150363164-Cyclohexyl-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 50 ml of water, 50 ml of ether and 10.0 g of 4-cyclohexylphenol, was added dropwise 12.6 ml of 60% nitric acid while cooling with ice. The temperature of the mixture was raised to room temperature and the reaction was carried out 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. The residue was purified by subjecting to silica-gel column-chromatography [eluent:chloroform] to give 6.92 g of 4-cyclohexyl-2-nitrophenol.

Workup

  1. temperaturewhile cooling with ice
  2. waitthe reaction was carried out 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
  8. customThe residue was purified

Sources & evidence

ORD record
ord-44f9c95b880548f2acd2cc9e4e80a416
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Reaction notes

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