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

HRID 1175059Notes

Reaction equation

HRID 1175059 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 11.0M 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-0ee1721bb59646f98c0ed99df8295109
Source dataset
uspto-grants-2010_11
Patent number
US07838595B2

Reaction notes

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