Sodium Iodide → Ethyl 6-iodohexanoate

HRID 857243Notes

Reaction equation

HRID 857243 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[I-:12].[Na+]>CC(C)=O>[I:12][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 10880140Ethyl 6-iodohexanoateYield 100.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 112 ml of a solution of 13.38 g of ethyl 6-bromohexanoate in acetone, 26.97 g of sodium iodide was added and heated to reflux for 18 hours. The reaction solution was cooled, filtered to remove insolubles and washed with acetone. The filtrate was concentrated and, after addition of water, extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous magnesium sulfate and concentrated to provide 16.21 g of the objective compound as red-yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction solution was cooled
  4. filtrationfiltered
  5. customto remove insolubles
  6. washwashed with acetone
  7. concentrationThe filtrate was concentrated
  8. additionafter addition of water
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with water and brine sequentially
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-ffe9aa70bcb941099e1ba9a1701d6c00
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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