Nitric Acid → 2,6-Diisopropyl-4-nitrophenol

HRID 1700271Notes

Reaction equation

HRID 1700271 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[C:9]=1[OH:17])([CH3:7])[CH3:6].C(OCC)(=O)C>C(O)(=O)C>[CH:14]([C:10]1[CH:11]=[C:12]([N+:1]([O-:4])=[O:2])[CH:13]=[C:8]([CH:5]([CH3:7])[CH3:6])[C:9]=1[OH:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 4943PropofolHCID 8857Ethyl Acetate

Product 1

HCID 106806032,6-Diisopropyl-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

78.3 mmol (4.93 g) of fuming nitric acid are added dropwise to a solution, cooled to 0° C., of 53.9 mmol (9.62 g) of 2,6-diisopropylphenol in 350 ml of acetic acid. The reaction mixture is stirred at 0° C. for 1 hour 30 minutes and is then poured into a mixture of ethyl acetate and ice. The organic phase is isolated and then washed with water. After drying and evaporating off the solvent, an oily residue is recovered which is purified by chromatography on silica gel using a petroleum ether: ethyl acetate mixture 9:1 as eluant.

Workup

  1. customThe organic phase is isolated
  2. washwashed with water
  3. customAfter drying
  4. customevaporating off the solvent
  5. customan oily residue is recovered which
  6. customis purified by chromatography on silica gel using a petroleum ether

Sources & evidence

ORD record
ord-383e14d5d7f04a7d8253f557b1ac75ca
Source dataset
uspto-grants-2002_02
Patent number
US06350759B1

Reaction notes

Loading…