Acetic Acid → HCID 86651064, compound

HRID 884945Notes

Reaction equation

HRID 884945 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([F:15])([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5].C(O)(=O)C.S(=O)(=O)(O)O.[N+:27]([O-])([OH:29])=[O:28]>O>[F:1][C:2]([F:16])([F:17])[C:3]([F:15])([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:27]([O-:29])=[O:28])[CH:9]=1)[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 42415504-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)phenol

Product 1

HCID 86651064HCID 86651064, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3.60 g of mixture containing 4-(heptafluoroisopropyl)phenol, 8 ml of acetic acid, and 2.5 g of concentrated sulfuric acid, a mixture of 1.05 g of 69% nitric acid and 1 ml of acetic acid was added dropwise while ice-cooling, and then stirred at room temperature for two hours. The reaction mixture was poured into water, and extracted with ethyl acetate three times. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.96 g of 4-(heptafluoroisopropyl)-2-nitrophenol.

Workup

  1. additionwas added dropwise while ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate three times
  4. washThe combined organic layers were washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad2f0937c25d42f1b9fc7e7adea86941
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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