Azobisisobutyronitrile → 12,12,13,13,14,14,15,15,15-Nonafluoropentadecan-1-ol

HRID 336068Notes

Reaction equation

HRID 336068 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.[C:13](I)([C:16]([C:19]([C:22]([F:25])([F:24])[F:23])([F:21])[F:20])([F:18])[F:17])([F:15])[F:14].[CH2:27]=[CH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38]>C(O)C.[Zn]>[C:13]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38])([C:16]([C:19]([C:22]([F:25])([F:24])[F:23])([F:21])[F:20])([F:18])[F:17])([F:15])[F:14]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 818510-Undecen-1-olHCID 67917Perfluorobutyl iodide

Product 1

HCID 2263051112,12,13,13,14,14,15,15,15-Nonafluoropentadecan-1-ol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

C4F9(CH2)11OAcr was prepared essentially as described above starting with the AIBN catalyzed addition of C4F9I to CH2═CH(CH2)9OH. The resulting iodohydrin was reduced with zinc in ethyl alcohol to give the desired C4F9(CH2)11OH and olefinic products in about an 80:20 ratio as follows.

Sources & evidence

ORD record
ord-6a98f5f53abe48b59d60b178906d2901
Source dataset
uspto-grants-2014_11
Patent number
US08889230B2

Reaction notes

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