Sodium Iodide → Ethyl 2-(6-iodohexyloxy)-2-methylpropionate

HRID 857245Notes

Reaction equation

HRID 857245 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[I-:17].[Na+]>CC(C)=O>[I:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 21866767Ethyl 2-(6-bromohexyloxy)-2-methylpropionate

Product 1

HCID 21866667Ethyl 2-(6-iodohexyloxy)-2-methylpropionateYield 102.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 76 ml of a solution of 12.16 g of ethyl 2-(6-bromohexyloxy)-2-methylpropionate in acetone, 18.52 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 14.46 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-c2b079df9a0b4058be9fb4bc5fe6654f
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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