Acetone → 11-iodoundecanoic Acid

HRID 217086Notes

Reaction equation

HRID 217086 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+].CC(C)=O>O>[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 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 1781211-Bromoundecanoic acid

Product 1

HCID 1146110411-iodoundecanoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11-Iodo undecanoic acid was synthesized according to Bergbreiter, J. Org. Chem., 40 (6), (1975) 779-782. Briefly, 250 g 11-Bromo undecanoic acid, 325 g Sodium iodide and 2 liter acetone were refluxed under N2 atmosphere for 24 hours. The mixture was divided and added to 4 liter H2O each. The mixtures were fritted and the crude product recrystallized from methanol and finally characterized by the melting point.

Workup

  1. customthe crude product recrystallized from methanol

Sources & evidence

ORD record
ord-24c6385fa7a54629aa097cd66d63737e
Source dataset
uspto-grants-2012_06
Patent number
US08193246B2

Reaction notes

Loading…