Nitric Acid → 2-Nitro-5-(trifluoromethyl)phenol

HRID 884926Notes

Reaction equation

HRID 884926 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[N+:12]([O-])([OH:14])=[O:13].C(=O)([O-])O.[Na+]>>[N+:12]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][C:5]=1[OH:9])([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 73763-(Trifluoromethyl)phenolHCID 516892Sodium Bicarbonate

Product 1

HCID 140916902-Nitro-5-(trifluoromethyl)phenol

Procedure

To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol.

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe combined organic layers washed with water
  3. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c7af4b3222d48cf902200474f373842
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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