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

HRID 1465484Notes

Reaction equation

HRID 1465484 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.O.C(=O)([O-])O.[Na+].[CH2:23](O)[CH3:24]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH2:23][CH3:24])=[O:6]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 676873-Fluoro-p-toluic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 13489923Benzoic acid, 3-fluoro-4-methyl-, ethyl esterYield 94.4%

Conditions

Temperature
0 °C

Procedure

To a solution of 3-fluoro-4-methylbenzoic acid (7.707 g, 50.00 mmol) in ethanol (35 ml) was added concentrated sulfuric acid (1.5 ml), and the mixture was heated under reflux for 6 hrs. The reaction mixture was cooled to 0° C., iced water and saturated aqueous sodium hydrogen carbonate were added, and the mixture was extracted twice with diethyl ether. The combined organic layer was washed twice with saturated aqueous sodium hydrogen carbonate and once with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give ethyl 3-fluoro-4-methylbenzoate (8.599 g, yield 94.4%) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. extractionthe mixture was extracted twice with diethyl ether
  4. washThe combined organic layer was washed twice with saturated aqueous sodium hydrogen carbonate and once with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea8d602805824c39af6763335c814d96
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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