Nitric Acid → 2-Isopropyl-4-nitrophenol

HRID 1268200Notes

Reaction equation

HRID 1268200 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].[N+:11]([O-])([OH:13])=[O:12].O>C(O)(=O)C>[CH:1]([C:4]1[CH:9]=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 69432-Isopropylphenol

Product 1

HCID 5289542-Isopropyl-4-nitrophenolYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-isopropylphenol (4.1 ml) in acetic acid (30 ml) was added 69% nitric acid (4 ml) in an ice bath and the mixture was stirred at the same temperature for 30 minutes. After addition of iced water, the reaction mixture was extracted with t-butyl methyl ether. The extractant was washed with water and brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/1 as an eluant to give the desired compound (2.66 g, yield 49%) as a yellow solid.

Workup

  1. extractionthe reaction mixture was extracted with t-butyl methyl ether
  2. washThe extractant was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-425b21d7ec7e4456bab2528b0a34dd38
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

Loading…