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

HRID 2047443Notes

Reaction equation

HRID 2047443 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.[C:24](=O)([O-])O.[Na+]>CO>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([O:16][CH3:24])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1235873,5-Bis(trifluoromethyl)phenylacetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 10401718Methyl 2-[3,5-bis(trifluoromethyl)phenyl]acetateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [3,5-bis(trifluoromethyl)phenyl]acetic acid (10 g) in methanol (50 mL) was added concentrated sulfuric acid (0.5 mL), and the mixture was stirred at 80° C. for 14 hr. The reaction mixture was cooled, basified with saturated aqueous sodium hydrogen carbonate solution, and concentrated under reduced pressure. The residue was diluted with ethyl acetate, and washed with saturated brine. The aqueous layer was extracted again with ethyl acetate, and the combined extract was dried, and concentrated to give methyl [3,5-bis(trifluoromethyl)phenyl]acetate (10.8 g, 100%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with saturated brine
  5. extractionThe aqueous layer was extracted again with ethyl acetate
  6. extractionthe combined extract
  7. customwas dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-740924888d54486d883aaf2b79afa587
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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