Sodium Iodide → 11-iodoundecanoic Acid

HRID 1780685Notes

Reaction equation

HRID 1780685 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[I-:15].[Na+]>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[I:15][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 1781211-Bromoundecanoic acid

Product 1

HCID 1146110411-iodoundecanoic Acid

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

To 11-bromoundecanoic acid dissolved in acetonitrile (50 ml) were added sodium iodide (2 g) and tetra-n-butylammonium iodide (1 g), and the mixture was heated under reflux for 4 hours. The reaction mixture was filtered, concentrated and distributed into ethyl acetate and water, and the ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated to give 11-iodoundecanoic acid (0.89 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. dry with materialthe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a3e41b2902a442a385e01447d1ed72f8
Source dataset
uspto-grants-1997_05
Patent number
US05631238

Reaction notes

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