Acetic Acid → 4-(Trifluoromethyl)phenol

HRID 2351113Notes

Reaction equation

HRID 2351113 reaction equation
O[C:2]1([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:6][C:5](=[O:8])[CH:4]=[CH:3]1.C(O)(=O)C.O>C(O)C.[Zn]>[F:10][C:9]([F:11])([F:12])[C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 138691094-Hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one

Product 1

HCID 678744-(Trifluoromethyl)phenolYield 84.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A solution of 200 mg (1.1 mmol) of 4-hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one in 1 mL of absolute ethanol was treated successively with 147 mg (2.2 mmol) of zinc dust and 1 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 20 mL of water. The resulting aqueous mixture was extracted with three 10 mL portions of diethyl ether. Combination, extraction with one 10 mL portion of 10% Na2CO3, drying (MgSO4), and concentration of the ether layers afforded a residue which was subjected to PTLC (one 2 mm silica gel plate eluted with dichloromethane), giving 151 mg (83% yield) of 4-trifluoromethylphenol.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. extractionThe resulting aqueous mixture was extracted with three 10 mL portions of diethyl ether
  4. extractionCombination, extraction with one 10 mL portion of 10% Na2CO3
  5. dry with materialdrying (MgSO4), and concentration of the ether layers
  6. customafforded a residue which
  7. washwas subjected to PTLC (one 2 mm silica gel plate eluted with dichloromethane)

Sources & evidence

ORD record
ord-e328cf62983741e4b9e4e0ee7bfae037
Source dataset
uspto-grants-1989_10
Patent number
US04871877

Reaction notes

Loading…