Potassium Hydroxide → 2-Methyl-3,4,6-trifluorobenzoic acid

HRID 2271268

Reaktionsgleichung

Reaktionsgleichung von HRID 2271268
[F:1][C:2]1[C:10](F)=[C:9]([F:12])[C:8]([F:13])=[C:7]([CH3:14])[C:3]=1[C:4]([OH:6])=[O:5].[OH-].[K+].NCCNCCNCCNCCNCCN.[H][H]>C(O)C.[OH-].[Pd+2].[OH-].O>[F:13][C:8]1[C:7]([CH3:14])=[C:3]([C:2]([F:1])=[CH:10][C:9]=1[F:12])[C:4]([OH:6])=[O:5]

Komponenten

8

Edukt 4

HCID 14797Potassium HydroxideHCID 19990PentaethylenehexamineHCID 129439972,3,4,5-Tetrafluoro-6-methylbenzoic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 101303052-Methyl-3,4,6-trifluorobenzoic acidAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1.04 g of 2,3,4,5-tetrafluoro-6-methylbenzoic acid in 15 ml of ethanol were added 840 mg of potassium hydroxide, 232 mg of pentaethylene hexamine and 200 mg of 20% palladium hydroxide. The mixture was stirred in a hydrogen atmosphere at room temperature for 3 hours. After addition of water, the reaction mixture was filtrated through celite and the filtrate was washed with diethyl ether. The aqueous layer was adjusted to pH 1 with concentrated hydrochloric acid and extracted with dichloromethane. After evaporating the solvent, the residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:3) to give 761 mg of 3,4,6-trifluoro-2-methylbenzoic acid (yield: 80%).

Aufarbeitung

  1. filtrationthe reaction mixture was filtrated through celite
  2. washthe filtrate was washed with diethyl ether
  3. extractionextracted with dichloromethane
  4. customAfter evaporating the solvent
  5. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-a963873675e54885aaadf31bcd845358
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06333431B1

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