Sulfuric Acid → 4-tert-Butyl-2-(trifluoromethyl)phenol

HRID 1834508Notes

Reaction equation

HRID 1834508 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[C:12](O)([CH3:15])([CH3:14])[CH3:13].S(=O)(=O)(O)O>FC(F)(F)C(O)=O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:5][C:4]=1[OH:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 679582-Trifluoromethylphenol

Product 1

HCID 126521024-tert-Butyl-2-(trifluoromethyl)phenol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2-trifluoromethylphenol (25 g., 0.15 moles), tert-butyl alcohol (12 g., 0.16 mole), trifluoroacetic acid (100 ml.) and 96% sulfuric acid (2 ml.) is stirred at about 20° C. for 48 hours. The mixture then is evaporated as far as possible under reduced pressure at 35°-40° C. The residue is dissolved in benzene (500 ml.) and the solution is washed with water, saturated NaHCO3 solution and saturated salt brine and dried over anhydrous MgSO4. The dried solution is again evaporated under reduced pressure and the temperature is finally raised to 140°-145° C. under 65 mm. pressure to remove unchanged 2-trifluoromethylphenol. The residue is distilled at 65 mm. after collecting a small fore-run (75% unchanged starting phenol and 25% product), 2-trifluoromethyl-4-(1,1-dimethylethyl)phenol (13.6 g.) is collected at 120°-132° C. as a pale pink oil that is 98% pure by gas liquid chromatography analysis and can be used directly in the next step.

Workup

  1. customThe mixture then is evaporated as far as possible under reduced pressure at 35°-40° C
  2. dissolutionThe residue is dissolved in benzene (500 ml.)
  3. washthe solution is washed with water, saturated NaHCO3 solution and saturated salt brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe dried solution is again evaporated under reduced pressure
  6. temperaturethe temperature is finally raised to 140°-145° C. under 65 mm
  7. custompressure to remove unchanged 2-trifluoromethylphenol
  8. distillationThe residue is distilled at 65 mm
  9. customafter collecting a small fore-run (75% unchanged starting phenol and 25% product), 2-trifluoromethyl-4-(1,1-dimethylethyl)phenol (13.6 g.)
  10. customis collected at 120°-132° C. as a pale pink oil that

Sources & evidence

ORD record
ord-972301ea49004ddc84719bc1c591222a
Source dataset
uspto-grants-1978_01
Patent number
US04070464

Reaction notes

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