1-Chloro-4-(trifluoromethyl)benzene → 1-Methoxy-4-(trifluoromethyl)benzene

HRID 397025Notes

Reaction equation

HRID 397025 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6](Cl)=[CH:5][CH:4]=1.[CH3:12][O-:13].[Na+]>CO>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([O:13][CH3:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 10942334Sodium Methoxide

Product 1

HCID 6006041-Methoxy-4-(trifluoromethyl)benzeneYield 57.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

200 g (1.11mol) of 4-(trifluoromethyl)chlorobenzene, 179 g (3.31 mol) of sodium methoxide, and 600 ml of methanol were mixed together in a pressurized reaction vessel, followed by stirring for 6 hr at 150° C. under tight sealing. The resulting reaction mixture was filtered to remove precipitates. Water was added to the obtained filtrate, followed by extraction with n-hexane. The resulting organic layer was washed with water, followed by drying with magnesium sulfate anhydride and removal of the solvent by distillation. The obtained residue was purified by distillation, thereby obtaining 112 g (0.636 mol) of 4-(trifluoromethyl)anisole (yield: 57%).

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered
  3. customto remove
  4. customprecipitates
  5. additionWater was added to the obtained filtrate
  6. extractionfollowed by extraction with n-hexane
  7. washThe resulting organic layer was washed with water
  8. dry with materialby drying with magnesium sulfate anhydride and removal of the solvent by distillation
  9. distillationThe obtained residue was purified by distillation

Sources & evidence

ORD record
ord-8bddc8a6be1f422cb06c541fe9551d09
Source dataset
uspto-grants-2003_08
Patent number
US06608217B2

Reaction notes

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