Ethanol → Ethyl 2-fluoro-3-methylbenzoate

HRID 1021248Notes

Reaction equation

HRID 1021248 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17][CH2:18]O>>[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27373792-Fluoro-3-methylbenzoic acid

Product 1

HCID 46311374Ethyl 2-fluoro-3-methylbenzoate

Conditions

Temperature
90 °C

Procedure

2-Fluoro-3-methylbenzoic acid (8.0 g) was mixed with EtOH (100 ml), and concentrated sulfuric acid was added thereto, followed by stirring at 90° C. overnight. The reaction mixture was concentrated under reduced pressure, and EtOAc and water were then added thereto. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, then dried over Na2SO4, and concentrated under reduced pressure to obtain ethyl 2-fluoro-3-methylbenzoate (7.84 g).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and EtOAc and water
  3. additionwere then added
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-71207a515886467c8efbd9f46606bb64
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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