Nitric Acid → HCID 14923120, compound

HRID 1064826Notes

Reaction equation

HRID 1064826 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([CH3:8])([CH3:7])[CH3:6]>C(#N)C.O>[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:1]([O-:4])=[O:2])[C:10]=1[OH:15])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 69232-Tert-Butylphenol

Product 1

HCID 14923120HCID 14923120, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Acetyl nitrate obtained by mixing acetyl anhydride (1.35 g, 13.3 mmol) with fuming nitric acid (13.3 mmol) at 0° C. was dropped into a solution of 2-tert-butylphenol (2.00 g, 13.3 mmol) in acetonitrile (30 ml) at −20° C. followed by stirring for 5 minutes. The reaction solution was diluted with water and extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (60 g of silica gel; developing solvent, hexane:acetone=3:1) to provide 600 mg (yield 23%) of 2-tert-butyl-6-nitrophenol as yellow crystals.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by a silica gel column chromatography (60 g of silica gel; developing solvent, hexane:acetone=3:1)

Sources & evidence

ORD record
ord-d3c12d7857a64fdaa7fe7fe88df7f7d6
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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