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

HRID 397026Notes

Reaction equation

HRID 397026 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.[CH3:12][O-:13].[Na+].CO>O>[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

5

Reactant 3

HCID 887MethanolHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 10942334Sodium Methoxide

Product 1

HCID 6006041-Methoxy-4-(trifluoromethyl)benzeneYield 62.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

100 g (0.445 mol) of 4-(trifluoromethyl)bromobenzene, 120 g (2.22 mol) of sodium methoxide, and 300 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 poured into water, 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 49 g (0.278 mol) of 4-(trifluoromethyl)anisole (yield: 62.6%).

Workup

  1. customThe resulting reaction mixture
  2. extractionfollowed by extraction with n-hexane
  3. washThe resulting organic layer was washed with water
  4. dry with materialby drying with magnesium sulfate anhydride and removal of the solvent by distillation
  5. distillationThe obtained residue was purified by distillation

Sources & evidence

ORD record
ord-410761a11f71492294eda8f396e9fe8b
Source dataset
uspto-grants-2003_08
Patent number
US06608217B2

Reaction notes

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