2,2-Diethoxyethanol → 1,1'-Oxybis(2,2-diethoxyethane)

HRID 1355371Notes

Reaction equation

HRID 1355371 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]>C1(C)C(C)=CC=CC=1>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Glycolaldehyde diethyl acetal (45.4 g, 338 mmol) was added dropwise to a stirred solution of sodium hydride (14.3 g, 60% dispersion in mineral oil, 357 mmol) in xylene (100 ml), and the reaction heated under reflux for 1 hour. The reaction mixture was cooled to room temperature and bromoacetaldehyde diethyl acetal (100 g, 507 mmol) was added. The resulting solution was heated under reflux for 20 hours, then cooled to room temperature. The solvent was removed under reduced pressure, and the residual solution was distilled under reduced pressure (80° C. @ 6 mm Hg), to afford the title compound as a colourless oil, 60.8 g.

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe resulting solution was heated
  4. temperatureunder reflux for 20 hours
  5. temperaturecooled to room temperature
  6. customThe solvent was removed under reduced pressure
  7. distillationthe residual solution was distilled under reduced pressure (80° C. @ 6 mm Hg)

Sources & evidence

ORD record
ord-0a65254ebd624fac88975dec0d601453
Source dataset
uspto-grants-2003_07
Patent number
US06586430B1

Reaction notes

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