Methanol → Methyl 5-fluoro-2-methylbenzoate

HRID 1987385Notes

Reaction equation

HRID 1987385 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-b2f66e5c15fa46e180d4259d626d4c0b
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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