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

Temperature

25 °C

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.

1. temperatureThe reaction mixture was cooled
2. additionUpon completion of addition
3. temperaturewhile maintaining the reaction mixture temperature at 25° C. or below
4. additionthis was also added dropwise
5. temperatureThe reaction mixture temperature was also maintained at 25° C. or below throughout the latter addition
6. additionUpon completion of addition
7. stirringstirring of the reaction mixture
8. concentrationto saturate the water layer
9. customThe organic layer was then decanted from the reaction mixture
10. dry with materialwas dried with magnesium sulfate
11. filtrationThe mixture was filtered
12. concentrationthe filtrate was concentrated under reduced pressure to a residual oil
13. distillationThe oil was distilled under reduced pressure

ORD record

ord-4c3bc77ef6e24cbda631f801b81a963b

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05081287