Iodoethane → 1-Ethoxy-3-(trifluoromethyl)benzene

HRID 1789629Notes

Reaction equation

HRID 1789629 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](C(C)=O)[CH3:8].C(I)C.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1>O>[CH2:7]([O:23][C:19]1[CH:18]=[C:17]([C:16]([F:24])([F:25])[F:15])[CH:22]=[CH:21][CH:20]=1)[CH3:8]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6569Methyl Ethyl Ketone2×HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium Carbonate

Product 1

HCID 184153071-Ethoxy-3-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (22.6 g) and then a mixture of methyl ethyl ketone (MEK) (150 mL) and ethyl iodide (47.8 g) were added to a mixture of MEK (310 mL) and 3-trifluoromethylphenol (a) (25.0 g) at room temperature, and the reaction mixture was heated and stirred for 2 hours. After returning the mixture to room temperature, water was added for liquid separation and the aqueous layer was extracted three times with diethyl ether. The organic layers were combined, washed with an 1 M aqueous sodium hydroxide solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 19.3 g of Compound (b).

Workup

  1. temperaturethe reaction mixture was heated
  2. customto room temperature
  3. extractionthe aqueous layer was extracted three times with diethyl ether
  4. washwashed with an 1 M aqueous sodium hydroxide solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e53b31a39b7e456887d2989addfbee81
Source dataset
uspto-grants-2006_07
Patent number
US07070838B2

Reaction notes

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