Sodium Iodide → 1,1-Diethoxy-2-iodoethane

HRID 2248589Notes

Reaction equation

HRID 2248589 reaction equation
C(=O)(O)[O-].[Na+].[I-:6].[Na+].Br[CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>CC(C)=O>[I:6][CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium Bicarbonate

Product 1

HCID 125047911,1-Diethoxy-2-iodoethane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of sodium bicarbonate (426.2 g, 5074 mmol) in acetone was added sodium iodide (760.3 g, 5074 mmol) and 2-bromo-1,1-diethoxyethane (500 g, 2537 mmol). The reaction mixture was allowed to reflux for 8 hours. The reaction mixture was then filtered and the solvent evaporated. Ether was added and the reaction mixture filtered again. The ether was evaporated, leaving the title compound, 2-iodo-1,1-diethoxyethane, as an oil, which was further purified by column chromatography.

Workup

  1. temperatureto reflux for 8 hours
  2. filtrationThe reaction mixture was then filtered
  3. customthe solvent evaporated
  4. additionEther was added
  5. filtrationthe reaction mixture filtered again
  6. customThe ether was evaporated

Sources & evidence

ORD record
ord-2d38f9ae2f9d4977985f1450025407d7
Source dataset
uspto-grants-1991_08
Patent number
US05041442

Reaction notes

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