Acetic Acid → 4-(Trifluoromethyl)phenol

HRID 1382009Notes

Reaction equation

HRID 1382009 reaction equation
C([Si](CCCC)(CCCC)O[C:7]1([C:14]([F:17])([F:16])[F:15])[CH:12]=[CH:11][C:10](=[O:13])[CH:9]=[CH:8]1)CCC.C(O)(=O)C.O>C(O)C.[Zn]>[F:15][C:14]([F:16])([F:17])[C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 14343496HCID 14343496, compound

Product 1

HCID 678744-(Trifluoromethyl)phenolYield 47%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A solution of 3.9 g (20 mmol) of 4-tri-n-butylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one in 10 mL of absolute ethanol was treated successively with 1.3 g (20 mmol) of zinc dust and 10 mL of a solution of 80% acetic acid - 20% water. The mixture was heated to reflux for one hour, allowed to cool to room temperature, and poured into 100 mL of water. The resulting aqueous mixture was extracted with three 50 mL portions of diethyl ether. Combination, drying (MgSO4), and concentration of the ether layers afforded a residue which purified by short path distillation at 5.0 torr. At 60°-65° C., 0.80 g (47% yield) of 4-trifluoromethylphenol was collected.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. extractionThe resulting aqueous mixture was extracted with three 50 mL portions of diethyl ether
  4. dry with materialCombination, drying (MgSO4), and concentration of the ether layers
  5. customafforded a residue which
  6. distillationpurified by short path distillation at 5.0 torr

Sources & evidence

ORD record
ord-36a5aecad80241458ff3de6f1590d227
Source dataset
uspto-grants-1989_02
Patent number
US04804773

Reaction notes

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