Ethylene Glycol → 2-(4,4-Diethoxy-butoxy)ethanol

HRID 658223Notes

Reaction equation

HRID 658223 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH2:16]([O:18][CH:19]([O:24][CH2:25][CH3:26])[CH2:20][CH2:21][CH2:22]Cl)[CH3:17]>>[CH2:16]([O:18][CH:19]([O:24][CH2:25][CH3:26])[CH2:20][CH2:21][CH2:22][O:3][CH2:2][CH2:1][OH:4])[CH3:17]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 6386tert-ButanolHCID 2625984-Chlorobutyraldehyde Diethyl AcetalHCID 23665647Potassium tert-butoxide

Product 1

HCID 230906432-(4,4-Diethoxy-butoxy)ethanol

Procedure

A mixture of anhydrous ethylene glycol (120 g, 1.93 moles), a 1.0M solution of potassium tert-butoxide in tert-butanol (70 ml, 0.07 moles), and 4-chlorobutyraldehyde diethyl acetal (11 g, 0.061 moles) is stirred overnight at 100° C. under an argon atmosphere. After cooling to room temperature, the reaction mixture is added to 600 ml distilled water. The product is extracted with dichloromethane (150, 125, and 125 ml). The combined extracts are then dried with anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg). Yield 5.5 g.

Workup

  1. additionthe reaction mixture is added to 600 ml
  2. distillationdistilled water
  3. extractionThe product is extracted with dichloromethane (150, 125, and 125 ml)
  4. dry with materialThe combined extracts are then dried with anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. distillationNext the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg)

Sources & evidence

ORD record
ord-925c66e6cea8476f9998c6b5a0ec55aa
Source dataset
uspto-grants-2011_12
Patent number
US08076412B2

Reaction notes

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