Water → HCID 68289756, compound

HRID 878776Notes

Reaction equation

HRID 878776 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.IC.[C:18](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:1][C:2]([F:14])([F:15])[O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:18])=[O:10])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 534068704-[(Trifluoromethoxy)methyl]benzoic acid

Product 1

HCID 68289756HCID 68289756, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(trifluoromethoxy)methyl]benzoic acid (500 mg, 2.27 mmol) in N,N-dimethylformamide (25 mL) were added iodomethane (300 μL, 4.82 mmol) and potassium carbonate (1000 mg, 7.24 mmol). The mixture was stirred at room temperature overnight, and then to the reaction solution was added water, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1→80:20) to give methyl 4-[(trifluoromethoxy)methyl]benzoate (453 mg, 85%) as a pale brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1→80:20)

Sources & evidence

ORD record
ord-b9666007783e44d0a15ad6bedcb2b4e7
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

Loading…