Acetone → Methyl 3-fluoro-2-methoxybenzoate

HRID 1165258Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165258
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5](O)=[O:6])[C:3]=1O.IC.[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH3:20]C(C)=O.[OH2:24]>>[F:1][C:2]1[C:3]([O:17][CH3:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:6][CH3:20])=[O:24]

Komponenten

6

Edukt 5

HCID 180AcetoneHCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2687243-Fluoro-2-hydroxybenzoic acid

Produkt 1

HCID 19862628Methyl 3-fluoro-2-methoxybenzoate

Versuchsvorschrift

A mixture containing 3-fluorosalicylic acid (20 g) [obtained as white crystals, m.p. 145°-147° C., by the method of L N Ferguson et alia, J.Amer.Chem.Soc., 1950, 72, 5315], iodomethane (60 g), potassium carbonate (40 g) and acetone (200 ml) was heated under reflux for 24 hours. Water (500 ml) was added and the mixture was extracted with ether (3×150 ml). The combined extracts were dried (MgSO4) and evaporated to give methyl 3-fluoro-2-methoxybenzoate (B) (21 g) as a yellow oil, which was used without further purification; NMR: 3.85 (3H,s), 3.95 (3H,s) and 6.8-7.6 (3H,m).

Aufarbeitung

  1. customobtained as white crystals, m.p. 145°-147° C., by the method of L N Ferguson et alia, J.Amer.Chem.Soc
  2. temperatureunder reflux for 24 hours
  3. extractionthe mixture was extracted with ether (3×150 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ba6defad96e244e392b8e5a6b7ec0a68
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04908380

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