[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]>C(O)C.[Pd]>[F:1][C:2]([F:16])([F:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]Dissolve 12,12,12-trifluoro-8-dodecenoic acid (1.39g, 5.5 mmol) in ethanol (50 mL) and place in a Paar hydrogenation flask. Add 10% palladium/carbon (500 mg). Charge the vessel to 50 psi and shake for 18 hours. Filter through celite and remove the solvent in vacuo to give 12,12,12-trifluorododecanoic acid.
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