Nitric Acid → 4-Butyl-2-nitrophenol

HRID 1723006Notes

Reaction equation

HRID 1723006 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1.[N+:12]([O-])([OH:14])=[O:13]>O>[CH2:4]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=1)[CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 154204-Butylphenol

Product 1

HCID 1043534-Butyl-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of 5.0 g of 4-n-butylphenol in 14 ml of water was added dropwise 3.7 ml of 70% nitric acid while cooling with ice and the temperature of the mixture was raised to room temperature and the reaction was carried out for 40 minutes. After 500 ml of water was added thereto, 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 subjected to silica-gel column-chromatography [eluent: ethyl acetate] to give 6.20 g of 4-n-butyl-2-nitrophenol.

Workup

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

Sources & evidence

ORD record
ord-db45d21590fb4755b87a16d674faeb85
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Reaction notes

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