Sodium Hydroxide → 6,6-Difluorohex-5-en-1-ol

To a stirred solution of 0.84 gram (0.0121 mole) of sodium hydroxide in 1.5 ml of water was added a solution of 3.3 grams (0.0121 mole) of 6,6-difluoro-5-hexenyl 4-chlorobenzoate (prepared in Example 19) in 20 ml of ethanol. Upon completion of addition, the reaction mixture was warmed to reflux where it was stirred for 18 hours. After this time the reaction mixture was cooled to ambient temperature, and it was concentrated under reduced pressure to a residual semi-solid. The semi-solid was taken up in water and diethyl ether. The aqueous layer was separated, and it was washed with two 100 ml portions of diethyl ether. The ether washes were combined with the organic layer, and the combination was washed in turn with one 50 ml portion of water and one 100 ml portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 1.6 grams of 6,6-difluoro-5-hexen-1-ol. The nmr spectrum was consistent with the proposed structure.

1. additionUpon completion of addition
2. temperaturethe reaction mixture was warmed
3. temperatureto reflux where it
4. concentrationit was concentrated under reduced pressure to a residual semi-solid
5. customThe aqueous layer was separated
6. washit was washed with two 100 ml portions of diethyl ether
7. washthe combination was washed in turn with one 50 ml portion of water and one 100 ml portion of an aqueous solution saturated with sodium chloride
8. dry with materialThe organic layer was dried with magnesium sulfate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-9ea8946c7d634d288ceaddbd87d33b1d

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05081287