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

HRID 884942Notes

Reaction equation

HRID 884942 reaction equation
[F:1][C:2]([F:14])([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)C>[F:1][C:2]([F:14])([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([N+:20]([O-:22])=[O:21])[CH:8]=1)[C:3]([F:5])([F:4])[F:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 10856782Phenol, 4-(pentafluoroethyl)-

Product 1

HCID 866510624-(Pentafluoroethyl)-2-nitrophenolYield 67.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 1.70 g of 4-(pentafluoroethyl)phenol, 6 ml of acetic acid and 2.0 ml of concentrated sulfuric acid, a mixture of 0.80 g of 69% nitric acid and 1 ml of acetic acid was added dropwise while ice-cooling, and stirred at room temperature for three hours. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate three times. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.40 g of 4-(pentafluoroethyl)-2-nitrophenol.

Workup

  1. additionwas added dropwise while ice-
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate three times
  4. washThe combined organic layers were washed with water
  5. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2983bdbabe042b4a0d1f6b20cb615d9
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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