Methanol → 4-[2-Chloro-4-(trifluoromethyl)phenoxy]phenol

HRID 1834356Notes

Reaction equation

HRID 1834356 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]CC2C=CC=CC=2)=[CH:15][CH:14]=1.CO.[H][H]>[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 13094093HCID 13094093, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 129406134-[2-Chloro-4-(trifluoromethyl)phenoxy]phenolYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Benzyloxyphenyl 2-chloro-4-trifluoromethylphenyl ether (25 g., 0.066 mole), purified by recrystallization from methanol, ethyl acetate (200 ml.) and 10% palladium on charcoal (1.0 g.) are charged to a 2-liter Paar hydrogenation bottle and shaken in a hydrogen atmosphere (40-45 psi) until hydrogen uptake ceases. The catalyst is then removed by filtration and the solvent and toluene are removed in vacuo to give 17.9 g. (94% yield) of 4-(2-chloro- 4-trifluoromethylphenoxy)phenol, mp 55°-6 ° C.

Workup

  1. additionare charged to a 2-liter Paar hydrogenation bottle
  2. customThe catalyst is then removed by filtration
  3. customthe solvent and toluene are removed in vacuo
  4. customto give 17.9 g

Sources & evidence

ORD record
ord-c0fce66254f945c18967c9b5fb128bc0
Source dataset
uspto-grants-1978_01
Patent number
US04070178

Reaction notes

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