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

HRID 1913705Notes

Reaction equation

HRID 1913705 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-737d55b4fd004ce3b2c5a3f89aee4c0a
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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