Acetic Acid → 9,9,10,10,11,11,12,12,12-Nonafluorododecan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a slurry of 98.0 g of zinc powder in 600 mL of ethanol was added 3.0 g of acetic acid. A solution of the crude 7-iodo-8-(nonafluorobutyl)-1-octanol prepared above in 100 mL of ethanol was added dropwise with stirring over 15 min, and the reaction mixture was heated at 50° C. for 3 hr. The mixture was filtered, and the filtrate was concentrated to 100.0 g of a viscous, light yellow fluid. A 79.6 g portion of this material was stirred with 300 mL of hexanes, and the supernatant was filtered through diatomaceous earth (marketed under the trade designation “CELITE” by Johns-Manville Corporation, Denver, Colo.) and concentrated to give 44.24 g of 8-(nonafluorobutyl)-1-octanol as a clear, colorless oil, which was used without further purification.

Provenance & Evidence