Methanol → HCID 21838228, compound

HRID 1740288Notes

Reaction equation

HRID 1740288 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=[O:13])[CH:5]=[C:6]([F:8])[CH:7]=1.S(=O)(=O)(O)O.[CH3:23]O>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([O:14][CH3:23])=[O:13])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 114248163-(3,5-difluorophenyl)benzoic Acid

Product 1

HCID 21838228HCID 21838228, compound

Procedure

To a mixture of 3-(3,5-difluorophenyl)benzoic acid (2.3 g) in anhydrous methanol (46 ml) was added concentrated sulfuric acid (2.3 ml). The mixture was heated under reflux for four hours. After cooling to ambient temperature, the mixture was concentrated. Ethyl acetate (200 ml) and water (100 ml) were added and the layers were separated. The organic layer was successively washed with 20% aqueous potassium carbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with hexane-ethyl acetate (10:1) as an eluent. The fractions containing the object product were collected and evaporated in vacuo to give methyl 3-(3,5-difluorophenyl)benzoate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for four hours
  3. concentrationthe mixture was concentrated
  4. additionEthyl acetate (200 ml) and water (100 ml) were added
  5. customthe layers were separated
  6. washThe organic layer was successively washed with 20% aqueous potassium carbonate solution and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel with hexane-ethyl acetate (10:1) as an eluent
  10. additionThe fractions containing the object product
  11. customwere collected
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-6ab58b8b04b847a28befafa750d5db8c
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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