Nitric Acid → 4-(4-Methoxycarbonylphenyl)-2-nitrophenol

HRID 413637Notes

Reaction equation

HRID 413637 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:8].O>C(O)(=O)C>[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([N+:1]([O-:4])=[O:2])[CH:16]=2)=[CH:11][CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

Product 1

HCID 185210364-(4-Methoxycarbonylphenyl)-2-nitrophenolYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated nitric acid (1.8 ml) was carefully added to a cooled suspension (5-10° C.) of phenol 27 (2.0 mg, 8.8 mmol) in 60 ml of glacial acetic acid. The reaction mixture was stirred for one hour and was then allowed to warm to room temperature and stirred for an additional 30 minutes. Water was added (50 ml) and the reaction mixture was cooled, filtered, and washed with water to yield a yellow powder. The crude product was purified via flash chromatography through a small pad of silica gel with elutions of 80/20 and 50/50 (Hex/EtOAc), respectively. Evaporation of the solvent yielded 2.23 g (93%) of a bright yellow solid.

Workup

  1. stirringstirred for an additional 30 minutes
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. washwashed with water
  5. customto yield a yellow powder
  6. customThe crude product was purified via flash chromatography through a small pad of silica gel with elutions of 80/20 and 50/50 (Hex/EtOAc)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8c196ee68dcb4e91a8968e9f8853e2bd
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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