Water → 12,12-Difluoro-11-dodecen-2-ol

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere 6.3 grams (0.02 mole) of mercuric acetate was placed in a reaction vessel. To this was added 20 ml of water and then 20 ml of tetrahydrofuran. The reaction mixture was cooled, and 4.0 grams (0.02 mole) of 1,1-difluoro-1,11-dodecadiene was added dropwise while maintaining the reaction mixture temperature at 25° C. or lower. Upon completion of addition, the reaction mixture was stirred for 20 minutes. After this time 20 ml of an aqueous 3 Molar solution of sodium hydroxide was added dropwise while maintaining the reaction mixture temperature at 25° C. or below. Sodium borohydride, 0.38 gram (0.01 mole), was dissolved in another 20 ml of the aqueous 3 Molar solution of sodium hydroxide, and this was also added dropwise. The reaction mixture temperature was also maintained at 25° C. or below throughout the latter addition. Upon completion of addition, stirring of the reaction mixture was stopped, and mercury was allowed to settle to the bottom of the reaction vessel. Sufficient sodium chloride was added to the reaction mixture to saturate the water layer. The organic layer was then decanted from the reaction mixture and was dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residual oil. The oil was distilled under reduced pressure, yielding 0.53 gram of 12,12-difluoro-11-dodecen-2-ol; b.p. 120° C./3.6 mm. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence