[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]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%).
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