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

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. NMR (d6-DMSO): 1.11 ppm (t, 6H), 1.53 ppm (m, —CH2CH, 2H), 1.64 ppm (m, —CH2CH2CH, 2H), 3.37 ppm (t, —O—CH9CH2CH2CH, 2H), 3.53 ppm (t, HO—CH2CH2O—, 2H), 3.62 ppm (q, —CH2CH3, 4H), 3.70 ppm (t, HO—CH2—, 2H), 4.38 ppm (t, —CH acetal, 1H), 4.54 ppm (t, 1H, —OH).

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)

ORD record

ord-c0da422494104a609d1b4b259b33afe7

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853325B2