Ethanol → Benzoic acid, 3-fluoro-4-methyl-, ethyl ester

HRID 1257458Notes

Reaction equation

HRID 1257458 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:22](O)[CH3:23]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH2:22][CH3:23])=[O:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 676873-Fluoro-p-toluic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 13489923Benzoic acid, 3-fluoro-4-methyl-, ethyl ester

Procedure

To a solution (50 mL) of 3-fluoro-4-methylbenzoic acid (5.0 g, 32 mmol) in ethanol was added conc. sulfuric acid (0.25 mL), and the mixture was heated under reflux overnight. The reaction mixture was allowed to cool to room temperature, and neutralized with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=80/20) to give the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. extractionextracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by column chromatography (hexane-hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-0a07b28ae6ba4068a2b2695145b101ab
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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