Guaiacol → 1-Methoxy-2-(2,2,2-trifluoroethoxy)benzene

HRID 273847Notes

Reaction equation

HRID 273847 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].[F:15][C:16]([F:20])([F:19])[CH2:17]I.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:17][C:16]([F:20])([F:19])[F:15]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethane

Product 1

HCID 200943441-Methoxy-2-(2,2,2-trifluoroethoxy)benzeneYield 71.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To dry N,N-dimethylformamide (10 ml) were added 2-methoxyphenol (150 mg), 2,2,2-trifluoroethyl iodide (584 mg) and potassium carbonate (400 mg), and the mixture was stirred vigorously at 130° C. for 6 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent to give 179 mg of 1-methoxy-2-(2,2,2-trifluoroethoxy) benzene as an oil.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by medium pressure liquid column chromatography on silica gel using
  6. additiona mixture of hexane and chloroform (5/2) as eluent

Sources & evidence

ORD record
ord-c99e62268a24476991407e3f62ee28a3
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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