Hydrochloric Acid → 2,2,3,3-Tetrafluoro-1-Hydroxy-4-n-Propylbicyclo[2.2.2]octane

HRID 1644129Notes

Reaction equation

[F:1][C:2]1([F:23])[C:7]([F:9])([F:8])[C:6]2([CH2:12][CH2:13][CH3:14])[CH2:10][CH2:11][C:3]1([O:15]C(CCCCC)=O)[CH2:4][CH2:5]2.[OH-].[K+].O.Cl>C(OCC)(=O)C.C(O)C>[F:1][C:2]1([F:23])[C:7]([F:9])([F:8])[C:6]2([CH2:12][CH2:13][CH3:14])[CH2:5][CH2:4][C:3]1([OH:15])[CH2:11][CH2:10]2

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,2,3,3-tetrafluoro-1-pentylcarbonyloxy-4-n-propylbicyclo[2.2.2]octane (11) (0.30 g), potassium hydroxide (0.10 g), water (0.5 mL), and ethanol (2.0 mL) was stirred at 70° C. for 20 minutes. The mixture was neutralized with hydrochloric acid, added with ethyl acetate (30 mL), and the organic layer was washed with aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then vaporized off under reduced pressure, to thereby obtain a crude product. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3:1), to thereby obtain 2,2,3,3-tetrafluoro-1-hydroxy-4-n-propylbicyclo[2.2.2]octane (12) (yield=0.20 g, yield ratio=94%) as a colorless clear solid.

Workup

washthe organic layer was washed with aqueous sodium hydrogen carbonate solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record: ord-83599814ad434dfebc9a69f2d48372ba
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124196B2

Reaction notes

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