Potassium Hydroxide → 3-Fluoro-4-(oxetan-3-yloxy)benzoic acid

HRID 1908106

Reaktionsgleichung

Reaktionsgleichung von HRID 1908106
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]1[CH2:16][O:15][CH2:14]1)[C:5]([O:7]C)=[O:6].[OH-].[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]1[CH2:14][O:15][CH2:16]1)[C:5]([OH:7])=[O:6]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 58550731Methyl 3-fluoro-4-(oxetan-3-yloxy)benzoate

Produkt 1

HCID 566044493-Fluoro-4-(oxetan-3-yloxy)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Crude methyl 3-fluoro-4-(oxetan-3-yloxy)benzoate from Step 1, MeOH (1 mL), and KOH (4.0 mL of 3.0 M, 12 mmol) were combined and the mixture was allowed to stir for 3 h at rt. The mixture was extracted with EtOAc and the organic layer was discarded. The aqueous layer was then treated with 1N HCl and the pH was adjusted to pH 3. The aqueous layer was extracted with EtOAc (3×) and the combined organic layers were dried over sodium sulfate and the solvent was removed. The crude acid was used without further purification. ESI-MS m/z calc. 212.1. found 213.0 (M+1)+; Retention time: 1.65 minutes (4 min run).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. additionThe aqueous layer was then treated with 1N HCl
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. customthe solvent was removed
  6. customThe crude acid was used without further purification
  7. customRetention time: 1.65 minutes (4 min run)

Quellen und Nachweise

ORD-Eintrag
ord-5dbcc214258a46c985cdbfb868cdd918
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598164B2

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