Réaction #2358450

Équation de réaction

hydrogen

2,3,4,5-tetrafluoro-6-methylbenzoic acid

potassium hydroxide

pentaethylene hexamine

→

3,4,6-trifluoro-2-methylbenzoic acid

Rendement 80.1%

Solvants

water

ethanol

Conditions de réaction

Traitement

1. 1
   Filtrationthe reaction mixture was filtrated through celite
2. 2
   Lavagethe filtrate was washed with diethyl ether
3. 3
   Extractionextracted with dichloromethane
4. 4
   AutreAfter evaporating the solvent
5. 5
   Autrethe residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:3)

Mode opératoire

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%).

Source