Ethanol → Ethyl 4-fluoro-2-hydroxybenzoate

HRID 1258175Notes

Reaction equation

HRID 1258175 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[CH2:16]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[OH:11])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 676614-Fluorosalicylic acid

Product 1

HCID 22478444Ethyl 4-fluoro-2-hydroxybenzoate

Procedure

To a solution of 4-fluoro-2-hydroxybenzoic acid (3.0 g) in ethanol (40 mL) was added thionyl chloride (5.61 mL) at 0° C., and the mixture was heated under reflux for 24 hours. The reaction mixture was concentrated under reduced pressure. This residue was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (3.5 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionThis residue was poured into water
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d1edebb732844dd59ee37d9115e84154
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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