Azobisisobutyronitrile → 6,6,7,7,8,8,9,9,9-Nonafluorononan-1-ol

HRID 898089Notes

Reaction equation

HRID 898089 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.I[CH:14]([CH2:19][C:20]([F:32])([F:31])[C:21]([F:30])([F:29])[C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[CH2:15][CH2:16][CH2:17][OH:18].P(O)(O)O.C(N(CC)CC)C>O1CCOCC1>[F:31][C:20]([F:32])([C:21]([F:29])([F:30])[C:22]([F:27])([F:28])[C:23]([F:24])([F:25])[F:26])[CH2:19][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 8471TriethylamineHCID 107909Phosphorous acidHCID 85830369HCID 85830369, compound

Product 1

HCID 154151756,6,7,7,8,8,9,9,9-Nonafluorononan-1-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of AIBN (4.9 g, 30 mmol) in dioxane (150 cm3) was added dropwise into a solution of 4iodo-6,6,7,7,8,8,9,9,9-nonafluorononan-1-ol (Preparation 1B, 25 g, 58 mmol), phosphorous acid (19.1 g, 0.29 mol) and triethylamine (32.3 g, 0.32 mol) in dioxane (150 cm3) under an atmosphere of nitrogen during reflux. After addition, the reaction mixture was refluxed for a period of time until the GLC analysis revealed a complete reaction (usually an hour). The crude product was extracted into diethyl ether (3×50 cm3) and dried (MgSO4). The solvent was removed in vacuo and the pure product was obtained by reduced pressure distillation as a colourless liquid.

Workup

  1. temperatureduring reflux
  2. additionAfter addition
  3. temperaturethe reaction mixture was refluxed for a period of time until the GLC analysis
  4. customa complete reaction (usually an hour)
  5. extractionThe crude product was extracted into diethyl ether (3×50 cm3)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe pure product was obtained by reduced pressure distillation as a colourless liquid

Sources & evidence

ORD record
ord-20f6b7d6954c4d52918c4cde540dc912
Source dataset
uspto-grants-2008_04
Patent number
US07351452B2

Reaction notes

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