Sodium Iodide → 10-Iododecanoic acid

HRID 1024534Notes

Reaction equation

HRID 1024534 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[I-:14].[Na+]>CC(C)=O>[I:14][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 14271210-Bromodecanoic Acid

Product 1

HCID 1267197910-Iododecanoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mechanically stirred solution of 10-bromodecanoic acid (50 g, 0.2 mol) in 1 L of acetone under nitrogen was added sodium iodide (238.7 g, 1.59 mol) and the resulting heterogeneous reaction mixture was allowed to stir at room temperature for 18 h. The thick reaction mixture was filtered through a pad of Celite 521, concentrated in vacuo to one-fifth volume and diluted with 1 L of brine. This was extracted with 4×250 mL of hexanes. The combined organic extracts were washed with 2×250 mL of freshly prepared 10% aqueous sodium thiosulfate, dried over sodium sulfate, concentrated in vacuo and vacuum dried to give iodo acid 2 (57.5 g, 98%) as a white solid:

Workup

  1. filtrationThe thick reaction mixture was filtered through a pad of Celite 521
  2. concentrationconcentrated in vacuo to one-fifth volume
  3. additiondiluted with 1 L of brine
  4. extractionThis was extracted with 4×250 mL of hexanes
  5. washThe combined organic extracts were washed with 2×250 mL of freshly prepared 10% aqueous sodium thiosulfate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo and vacuum
  8. customdried

Sources & evidence

ORD record
ord-e8ae99eb60e44b299d62596450b4ab49
Source dataset
uspto-grants-2014_05
Patent number
US08722910B2

Reaction notes

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