Methanol → Methyl 3-fluoro-2-hydroxybenzoate

HRID 713047

Reaktionsgleichung

Reaktionsgleichung von HRID 713047
[F:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16]O>>[F:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:16])=[O:6]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2687243-Fluoro-2-hydroxybenzoic acid

Produkt 1

HCID 573875Methyl 3-fluoro-2-hydroxybenzoateAusbeute 94 %

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 3-fluoro-2-hydroxy-benzoic acid (5.0 g, 32 mmol) in methanol (20 mL) was added thionyl chloride (5.0 g, 42 mmol) dropwise and the reaction mixture was stirred at 40° C. for 3 hours, then heated at 50° C. for 16 hours. The reaction mixture was cooled and concentrated in vacuo and resulting residue was purified by silica gel column chromatography using 0-50% ethyl acetate/hexanes mixtures as eluant to give methyl 3-fluoro-2-hydroxy-benzoate (5.1 g, 94%) as white crystals. ESI-MS m/z calc. 170.0. found 170.9 (M+1)+; Retention time: 1.33 minutes (3 min run).

Aufarbeitung

  1. temperatureheated at 50° C. for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customresulting residue
  5. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7337c420c52a4a328726af9b0ff9f066
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181273B2

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