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

HRID 2416970Notes

Reaction equation

C(O)(=O)C.I[CH:6]([CH2:14][C:15]([F:27])([F:26])[C:16]([F:25])([F:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]>C(O)C.[Zn]>[F:22][C:17]([F:23])([C:18]([F:19])([F:20])[F:21])[C:16]([F:24])([F:25])[C:15]([F:27])([F:26])[CH2:14][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

additionwas added dropwise
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated to 100.0 g of a viscous, light yellow fluid
stirringA 79.6 g portion of this material was stirred with 300 mL of hexanes
filtrationthe supernatant was filtered through diatomaceous earth (
concentration) and concentrated

Sources & evidence

ORD record: ord-9894a04ac09e47aab2bbafe5315b097e
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06824882B2

Reaction notes

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