Methanol → Methyl 5-fluoro-2-methylbenzoate

HRID 1784216Notes

Reaction equation

HRID 1784216 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:17]O>>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[CH3:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1821145-Fluoro-2-methylbenzoic acid

Product 1

HCID 23555748Methyl 5-fluoro-2-methylbenzoateYield 78%

Procedure

5-Fluoro-2-methyl-benzoic acid (0.29 g, 1.9 mmol) was dissolved in anhydrous MeOH (7 mL) and c. H2SO4 (0.12 mL, 2.3 mmol) was added, heating to reflux for 16 hours. The solution was cooled to room temperature and partitioned between EtOAc (15 mL) and brine (10 mL). After separating, the aqueous phase was extracted with EtOAc (2×10 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to afford 5-fluoro-2-methyl-benzoic acid methyl ester as a pale brown liquid (0.25 g, 78%).

Workup

  1. temperatureheating
  2. temperatureto reflux for 16 hours
  3. custompartitioned between EtOAc (15 mL) and brine (10 mL)
  4. customAfter separating
  5. extractionthe aqueous phase was extracted with EtOAc (2×10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e7597cbdb5847fba435581e46e3fceb
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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