Hydrochloric Acid → Methyl 4-fluoro-3-methylbenzoate

HRID 1665239Notes

Reaction equation

HRID 1665239 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].Cl.[CH3:13]O>>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH3:11])[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2428284-Fluoro-3-methylbenzoic acid

Product 1

HCID 18788764Methyl 4-fluoro-3-methylbenzoateYield 83.7%

Procedure

To a solution of 4-fluoro-3-methylbenzoic acid (5.0 g, 32.4 mmol) in methanol (150 mL) was added concentrated hydrochloric acid (2 mL). The mixture was refluxed for 4 hrs and then concentrated. The residue was treated with ether (200 mL) and washed with water, 10% sodium hydroxide solution, water and finally brine. The organic layer was dried over sodium sulfate and solvents were removed to give 4-fluoro-3-methylbenzoic acid methyl ester (4.56 g, 83.7%) as an off-white solid.

Workup

  1. temperatureThe mixture was refluxed for 4 hrs
  2. concentrationconcentrated
  3. additionThe residue was treated with ether (200 mL)
  4. washwashed with water, 10% sodium hydroxide solution, water and finally brine
  5. dry with materialThe organic layer was dried over sodium sulfate and solvents
  6. customwere removed

Sources & evidence

ORD record
ord-d674b20a2cbf4033b24c92907551f199
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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