Methanol → Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].S(Cl)(Cl)=O.[CH3:17]O>>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:17])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]Participants
4
Conditions
- Temperature
- 85 °C
Procedure
(3-Fluoro-4-hydroxy-phenyl)-acetic acid (25 g, 150 mmol) was dissolved in methanol (100 mL), and thionyl chloride (5 mL) was added dropwise to the solution. The solution was heated to 85° C. for 16 hours. The reaction mixture was allowed to cool and evaporated to dryness in vacuo. The residue was partitioned between ethyl acetate and saturated NaHCO3. The organic layer was dried over MgSO4, filtered, and the filtrate was evaporated to dryness under reduced pressure to yield the crude title compound as an off white solid (25.3 g). 1H NMR (500 MHz, CDCl3): δ 7.07 (d, J=7.07 Hz, 1H), 7.00-6.97 (m, 2H), 3.74 (s, 3H), 3.73 (s, 2H).
Workup
- temperatureto cool
- customevaporated to dryness in vacuo
- customThe residue was partitioned between ethyl acetate and saturated NaHCO3
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customthe filtrate was evaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-38ad7895c2e4461eadadd4ae323b9322
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999991B2
Reaction notes
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