Potassium Iodide → 1,1'-Oxybis(2,2-diethoxyethane)

HRID 1739773

Reaction equation

HRID 1739773 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][OH:6])[CH3:2].[H-].[Na+].[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16]Br)[CH3:13].[I-].[K+]>O1CCCC1.O>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][O:6][CH2:16][CH:15]([O:18][CH2:19][CH3:20])[O:14][CH2:12][CH3:13])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 121292,2-DiethoxyethanolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 926201,1'-Oxybis(2,2-diethoxyethane)

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hydroxyacetaldehyde diethylacetal (3.75 g) was added to sodium hydride (0.8 g, 80% in mineral oil) in tetrahydrofuran (100 ml) under an atmosphere of nitrogen. The mixture was stirred and bromoacetaldehyde diethyl acetal (5.0 g) and potassium iodide (0.1 g) were added. The mixture was heated to reflux for 16 hours, water added and evaporated under reduced pressure. The residue was dissolved in diethyl ether, the organic phase washed with water, dried (MgSO4) and evaporated under reduced pressure to give bis(2,2-diethoxyethyl)ether, 3.43 g, as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washthe organic phase washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d18f2ce5649c497b8892fb78a99ce117
Source dataset
uspto-grants-1999_10
Patent number
US05968947

Linked notes

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