Nitric Acid → 2-Nitro-4-propylphenol

HRID 1723002Notes

Reaction equation

HRID 1723002 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[N+:11]([O-])([OH:13])=[O:12]>O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 125804-Propylphenol

Product 1

HCID 2405532-Nitro-4-propylphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 10.0 g of 4-n-propylphenol in 50 ml of water was added dropwise 11.0 ml of 61% nitric acid while cooling with ice, the temperature of mixture was raised to room temperature and the reaction was carried out for 2 hours. The reaction mixture was extracted with 300 ml of ethyl acetate, washed with a brine 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 8.69 g of 4-n-propyl-2-nitrophenol.

Workup

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

Sources & evidence

ORD record
ord-68242a53b8f4499da31af5fca05675fe
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Reaction notes

Loading…