Sodium Hydroxide → 3-Fluoro-4-isopropoxybenzoic acid

HRID 1405385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405385
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([OH:7])=[O:6]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 58551191Methyl 3-fluoro-4-isopropoxybenzoate

Produkt 1

HCID 179028843-Fluoro-4-isopropoxybenzoic acidAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl 3-fluoro-4-isopropoxybenzoate (from step 1), 1,4-dioxane (31 mL), and NaOH (31 mL of 1.0 M, 31 mmol) were combined and the mixture was heated at 80° C. for 20 min. The solvent was evaporated under reduced pressure. The crude mixture was dissolved in water and was washed with EtOAc (3×). The combined organics were discarded. The aqueous layer was acidified and was extracted with EtOAc (3×). The organic layer was dried over sodium sulfate, filtered and the concentrated under reduced pressure to yield 3-fluoro-4-isopropoxy-benzoic acid (1.25 g, 72%) as a white solid. ESI-MS m/z calc 198.1, found 199.3 (M+1)+. Retention time: 1.34 minutes (3 min run).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe crude mixture was dissolved in water
  3. washwas washed with EtOAc (3×)
  4. extractionwas extracted with EtOAc (3×)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-53223c5f8f2748d1b8d415487a72a6c6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916565B2

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