4-Benzyloxybenzotrifluoride → 4-(Trifluoromethyl)phenol

HRID 1863263Notes

Reaction equation

HRID 1863263 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[F:16][C:15]([F:17])([F:18])[C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 27981684-BenzyloxybenzotrifluorideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 678744-(Trifluoromethyl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 390 g. of 4-trifluoromethylphenyl benzyl ether in 3580 ml. of ethanol was placed in a low pressure hydrogenation vessel along with 30 g. of 5 percent palladium-on-carbon. An initial hydrogen pressure of 60 psi was used and the solution was hydrogenated at room temperature until the theoretical uptake of hydrogen had been achieved--about 2 hours. The catalyst was removed by filtration. Concentration of the filtrate yielded 4-trifluoromethylphenol, distilling in the range 51°-54° C. at 6 torr. Yield=212 gms. (84.5 percent).

Workup

  1. customabout 2 hours
  2. customThe catalyst was removed by filtration

Sources & evidence

ORD record
ord-328161224b5440f0b9296079639b3a53
Source dataset
uspto-grants-1979_09
Patent number
US04168388

Reaction notes

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