Methanol → Methyl 2-[3,5-bis(trifluoromethyl)phenyl]acetate

HRID 11780Notes

Reaction equation

HRID 11780 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.S(=O)(=O)(O)O.[CH3:24]O>>[CH3:24][O:15][C:14](=[O:16])[CH2:13][C:5]1[CH:4]=[C:3]([C:2]([F:17])([F:18])[F:1])[CH:8]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1235873,5-Bis(trifluoromethyl)phenylacetic acid

Product 1

HCID 10401718Methyl 2-[3,5-bis(trifluoromethyl)phenyl]acetate

Procedure

To a solution of 3,5-bis-trifluoromethylphenylacetic acid (3.0 g, 11.03 mmol) (Aldrich) in methanol (20 mL) was added concentrated sulfuric acid (1.0 mL) and the reaction mixture was heated at reflux overnight. The reaction mixture was concentrated in vacuo. The residue was then diluted with ethyl acetate (100 mL) and successively washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography to give 3,5-bis-trifluoromethylphenylacetic acid methyl ester as a colorless oil. (Yield 2.27 g, 72.1%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionThe residue was then diluted with ethyl acetate (100 mL)
  5. washsuccessively washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-410bce6426de4dcc9092dfffbf90a523
Source dataset
uspto-grants-2006_08
Patent number
US07098332B2

Reaction notes

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