Methanol → Methyl 2-fluoro-4-methylbenzoate

HRID 1879400Notes

Reaction equation

HRID 1879400 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27361452-Fluoro-4-methylbenzoic acid

Product 1

HCID 18759805Methyl 2-fluoro-4-methylbenzoate

Procedure

15.4 g of 2-fluoro-4-methylbenzoic acid was dissolved in 200 mL of methanol, and 10.0 mL of concentrated sulfuric acid was added thereto, followed by heating with reflux overnight. The reaction liquid was cooled to room temperature and then concentrated to about 50 mL, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 90:10) to obtain 15.2 g of methyl 2-fluoro-4-methylbenzoate.

Workup

  1. temperatureby heating
  2. temperaturewith reflux overnight
  3. customThe reaction liquid
  4. concentrationconcentrated to about 50 mL, and water
  5. additionwas added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 90:10)

Sources & evidence

ORD record
ord-fc2a36d82776437fa6f12f0b345ba07a
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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