Ethanol → Ethyl 5-fluoro-2-hydroxybenzoate
Reaction equation
[F:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH2:12](O)[CH3:13]>S(=O)(=O)(O)O>[CH2:12]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[OH:11])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 5-fluorosalicylic acid (50 g) in absolute ethanol (500 ml), concentrated sulfuric acid (10 ml) was cautiously added. The solution was heated at 90° C. for 72 hours. The solvent was removed in vacuo, and the viscous residue was made basic (final pH=9) by portionwise addition of saturated aqueous sodium bicarbonate. The solution was then extracted with three 200 ml portions of methylene chloride. The combined organic extracts were dried (anhydrous sodium sulfate) and concentrated in vacuo to afford the title compound (quantitative yield) as a viscous colorless oil.
Workup
- customThe solvent was removed in vacuo
- additionby portionwise addition of saturated aqueous sodium bicarbonate
- extractionThe solution was then extracted with three 200 ml portions of methylene chloride
- dry with materialThe combined organic extracts were dried (anhydrous sodium sulfate)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-583f8b9011bc49febf7b6d594317f3c1
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06887905B2
Reaction notes
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