M-Cresol → HCID 22262145, compound

HRID 1610346Notes

Reaction equation

HRID 1610346 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[F:9][C:10]([F:14])([F:13])[CH2:11]I.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:9][C:10]([F:14])([F:13])[CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 342M-CresolHCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethane

Product 1

HCID 22262145HCID 22262145, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-hydroxytoluene (5.0 g, 46.2 mmol) in N,N-dimethylformamide (50 ml) were added 2,2,2-trifluoro-1-iodoethane (10.7 g, 50.9 mmol) and potassium carbonate (12.8 g, 92.5 mmol) and the mixture was stirred overnight at 80° C. The reaction solution was diluted with water (200 ml) and extracted with diethyl ether (300 ml×2). The extract was washed successively with water and saturated brine, dried-over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 3-(2,2,2-trifluoroethoxy)toluene (7.60 g, 86%) as a colorless oil.

Workup

  1. extractionextracted with diethyl ether (300 ml×2)
  2. washThe extract was washed successively with water and saturated brine, dried-over anhydrous magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-4ff4f77a87ec429eba1044dc9e446394
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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