Nitric Acid → 2-Nitro-4-(propan-2-yl)phenol

HRID 1723004

Reaction equation

HRID 1723004 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[N+:11]([O-])([OH:13])=[O:12]>O>[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 74654-Isopropylphenol

Product 1

HCID 5289662-Nitro-4-(propan-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of 5.0 g of 4-hydroxycumene in 14 ml of water was added dropwise 4.0 ml of 70% nitric acid while cooling with ice and the temperature of 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 purified by subjecting silica-gel column-chromatography [eluent: ethyl acetate]to give 5.07 g of 4-isopropyl-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
  7. customThe residue was purified

Sources & evidence

ORD record
ord-87a08d2316084763b5539baff75a31f3
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Linked notes

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