Methanol → Methyl 3,4-difluoro-2-hydroxybenzoate

HRID 245525Notes

Reaction equation

HRID 245525 reaction equation
[F:1][C:2]1[C:3]([OH:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>O>[F:1][C:2]1[C:3]([OH:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([O:7][CH3:18])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27582863,4-Difluoro-2-hydroxybenzoic acid

Product 1

HCID 46311128Methyl 3,4-difluoro-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3,4-difluoro-2-hydroxybenzoic acid (6.45 g, 37.05 mmol) and sulfuric acid (6 ml, 113 mmol) in MeOH (25 ml) was heated at reflux overnight. The mixture was diluted with water and extracted with ether. The ether was washed with aqueous NaHCO3, water and brine. The combined aqueous layers were twice more extracted with ether, which was washed with NaHCO3, water, and brine. The combined ether extracts were dried (MgSO4) and concentrated to give 6.4 g of product as a white solid.

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with ether
  3. washThe ether was washed with aqueous NaHCO3, water and brine
  4. extractionThe combined aqueous layers were twice more extracted with ether, which
  5. washwas washed with NaHCO3, water, and brine
  6. dry with materialThe combined ether extracts were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f5c6c7fa9aa14ced8a7b636a22e0ea39
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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