Nitric Acid → 4-Nitro-3,5-bis(trifluoromethyl)phenol

HRID 1373732Notes

Reaction equation

HRID 1373732 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[F:5][C:6]([F:19])([F:18])[C:7]1[CH:8]=[C:9]([OH:17])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1>C(O)(=O)C>[N+:1]([C:8]1[C:7]([C:6]([F:5])([F:18])[F:19])=[CH:12][C:11]([C:13]([F:14])([F:15])[F:16])=[CH:10][C:9]=1[OH:17])([O-:4])=[O:2].[N+:1]([C:12]1[C:7]([C:6]([F:18])([F:19])[F:5])=[CH:8][C:9]([OH:17])=[CH:10][C:11]=1[C:13]([F:15])([F:14])[F:16])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 676803,5-Bis(trifluoromethyl)phenol

Product 2

HCID 210755992-Nitro-3,5-bis(trifluoromethyl)phenolHCID 210756024-Nitro-3,5-bis(trifluoromethyl)phenolYield 59.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Fuming nitric acid (8.22 mL, 198.2 mmol) was added dropwise to a solution of 3,5-bis(trifluoromethyl)phenol (28.5 g, 123.9 mmol) in acetic acid (300 mL) at about 10° C. After being elevated to room temperature, the mixture was stirred for 43 hours. The reaction mixture was poured into ice water and the resulting solution was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated saline, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (developing solvent; hexane:acetone=15:1→10:1) to yield a crude product. The crude product thus obtained was subjected to sublimation separation under reduced pressure (3 mmHg) at 80° C. by using an evaporator to distill off the isomer, that is, 2-nitro-3,5-bis(trifluoromethyl)phenol, whereby 10.1 g (yield: 29.7%) of 4-nitro-3,5-bis(trifluoromethyl)phenol was obtained as yellow needle-like crystals.

Workup

  1. customAfter being elevated to room temperature
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed successively with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column (developing solvent; hexane:acetone=15:1→10:1)
  8. customto yield a crude product
  9. customThe crude product thus obtained
  10. customwas subjected to sublimation separation under reduced pressure (3 mmHg) at 80° C.
  11. customan evaporator
  12. distillationto distill off the isomer

Sources & evidence

ORD record
ord-ab342dc5df01417488f4ca28541588f7
Source dataset
uspto-grants-2007_01
Patent number
US07163944B2

Reaction notes

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