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

HRID 1627377Notes

Reaction equation

HRID 1627377 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].O=S(Cl)Cl.[CH3:16][CH2:17]O>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH2:16][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 676873-Fluoro-p-toluic acid

Product 1

HCID 13489923Benzoic acid, 3-fluoro-4-methyl-, ethyl esterYield 96%

Conditions

Temperature
60 °C

Procedure

To a solution of 3-fluoro-4-methylbenzoic acid (13.23 g, 85.85 mmol) in EtOH (200 mL) at 0° C. was added SOCl2 (3 mL) dropwise. The reaction mixture was heated at 60° C. overnight, then cooled to room temperature, concentrated under reduced pressure and diluted with DCM. The organic layer was washed with 1N NaOH (100 mL×2), dried (MgSO4) and concentrated to give ethyl 3-fluoro-4-methylbenzoate (15.02 g, 96%).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with DCM
  4. washThe organic layer was washed with 1N NaOH (100 mL×2)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4f4f0fc4dc27456fbbb52b97ca07dc96
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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