Acetic Acid → 12,12,13,13,14,14,15,15,15-Nonafluoropentadecan-1-ol

HRID 2416974Notes

Reaction equation

C(O)(=O)C.I[CH:6]([CH2:17][C:18]([F:30])([F:29])[C:19]([F:28])([F:27])[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16]>C(O)C.[Zn]>[F:25][C:20]([F:26])([C:21]([F:22])([F:23])[F:24])[C:19]([F:27])([F:28])[C:18]([F:30])([F:29])[CH2:17][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16]

Participants

Conditions

Temperature: 50 °C

Procedure

To a slurry of 130.0 g of zinc powder in 500 mL of ethanol was added 5.0 g of acetic acid. A solution of 230.0 g of the crude 10-iodo-11-(nonafluorobutyl)-1-undecanol prepared above in 100 mL of ethanol was added dropwise with stirring over 1 hr. Then, the reaction mixture was heated at 50° C. for 4 hr. The mixture was filtered, and the filtrate was concentrated to a viscous, light yellow liquid. Bulb-to-bulb distillation of the liquid, in several portions, provided 97.3 g of 11-(nonafluorobutyl)-1-undecanol as a colorless solid, b.p. 160-200° C. at 0.05 torr (7 Pa).

Workup

additionwas added dropwise
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated to a viscous, light yellow liquid
distillationBulb-to-bulb distillation of the liquid

Sources & evidence

ORD record: ord-7f8963f5f68e454c905da05cfc1f2f50
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06824882B2

Reaction notes

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