[F:1][C:2]([F:17])=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14].[OH-].[Na+].Cl>O>[F:1][C:2]([F:17])=[CH: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]A mixture of 1.0 gram (0.004 mole) of methyl 12,12-difluoro-11-dodecenoate and 0.16 gram (0.004 mole) of powdered sodium hydroxide was stirred at ambient temperature for 16 hours. A few drops of water were added to the reaction mixture, and it was warmed to 75° C. where it stirred for 3-4 hours. The reaction mixture was cooled to ambient temperature, diluted with water and acidified to pH with aqueous 6N hydrochloric acid. The mixture was extracted with three portions of diethyl ether. The combined extracts were washed with an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 0.9 gram of 12,12-difluoro-11-dodecenoic acid. The nmr spectrum was consistent with the proposed structure.
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