Nitric Acid → HCID 22272691, compound

HRID 1064828Notes

Reaction equation

HRID 1064828 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[C:8]([CH:14]([CH3:16])[CH3:15])[CH:7]=1>C(#N)C.O>[Cl:5][C:6]1[CH:7]=[C:8]([CH:14]([CH3:15])[CH3:16])[C:9]([OH:13])=[C:10]([N+:1]([O-:4])=[O:2])[C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 69826-Chlorothymol

Product 1

HCID 22272691HCID 22272691, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Acetyl nitrate obtained by mixing acetyl anhydride (1.12 g, 11 mmol) with fuming nitric acid (693 mg, 11 mmol) at 0° C. was dropped into a solution of 4-chloro-2-isopropyl-5-methylphenol (1.84 g, 10 mmol) in acetonitrile (20 ml) at 0° C. followed by stirring for 50 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 (80 g of silica gel; developing solvent, hexane:methylene chloride=30:1→10:1) to provide 1.88 g (yield 83%) of 4-chloro-6-isopropyl-3-methyl-2-nitrophenol as pale 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 (80 g of silica gel; developing solvent, hexane:methylene chloride=30:1→10:1)

Sources & evidence

ORD record
ord-63207803679e4782b670b623a9412ab1
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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