Methanol → HCID 118468383, compound
Reaction equation
[F:1][C:2]1[C:3]([OH:12])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[F:1][C:2]1[C:3]([OH:12])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:18])=[O:6]Participants
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 3-fluoro-2-hydroxy-4-methylbenzoic acid (24.3 g) in methanol (500 mL) was added sulfuric acid (7.60 mL) at room temperature, and the mixture was stirred at 60° C. for 3 days. The solvent was evaporated under reduced pressure, and ethyl acetate and saturated brine were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the residue was added diisopropyl ether (50 mL), and the insoluble substance was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (25.4 g).
Workup
- customThe solvent was evaporated under reduced pressure, and ethyl acetate and saturated brine
- additionwere added
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washThe combined organic layers were washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- additionTo the residue was added diisopropyl ether (50 mL)
- customthe insoluble substance was removed by filtration
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d2b91b34bc67489c9f7cb26b73765893
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315458B2
Reaction notes
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