3-Trifluoromethyl-4'-benzyloxy-alpha-ethyl-benzhydrol → 3-Trifluoromethyl-4'-hydroxy-alpha-ethylbenzhydrol

HRID 1981558Notes

Reaction equation

HRID 1981558 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[C:6]([CH2:22][CH3:23])([OH:21])[C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1.[H][H]>[Pd].CO>[F:1][C:2]([F:27])([F:28])[C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[C:6]([CH2:22][CH3:23])([OH:21])[C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 202398663-Trifluoromethyl-4'-benzyloxy-alpha-ethyl-benzhydrolHCID 178418361HCID 178418361, compound

Product 1

HCID 1818763-Trifluoromethyl-4'-hydroxy-alpha-ethylbenzhydrol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

54.1 g. of 3-trifluoromethyl-4'-benzyloxy-α-ethyl-benzhydrol in 541 ml. of methanol are hydrogenated under atmospheric pressure, in the presence of 27.1 g. of a 10% palladium-on-charcoal catalyst. When the uptake of the calculated amount of hydrogen is complete, the catalyst is filtered off, and the solvent is distilled off under reduced pressure. The crude product is decoloured with charcoal in ethyl acetate, and recrystallized from a mixture of ethyl acetate and n-hexane. 30.8 g. of the named compound are obtained, melting at 102.5° to 103° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. distillationthe solvent is distilled off under reduced pressure
  3. customrecrystallized from a mixture of ethyl acetate and n-hexane
  4. customof the named compound are obtained

Sources & evidence

ORD record
ord-7fc03fb4c9b04d1a902be11de0f1e52a
Source dataset
uspto-grants-1986_06
Patent number
US04593047

Reaction notes

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