Sodium Iodide → 11-iodoundecanoic Acid
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
Product 1
Reagents, catalysts & solvents 2
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
- temperaturethe mixture was heated
- temperatureunder reflux for 4 hours
- filtrationThe reaction mixture was filtered
- concentrationconcentrated
- dry with materialthe ethyl acetate layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a3e41b2902a442a385e01447d1ed72f8
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05631238
Reaction notes
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