Ethylene Glycol → 2-(2,2-Dimethoxyethoxy)ethan-1-ol

Temperature

115 °C

Potassium hydroxide (30 g, 0.51 mol) was suspended in ethylene glycol (100 ml) and the mixture was heated to 115° C. with stirring. After the KOH dissolved completely, 2-chloro-1,1-dimethoxy-ethane (30.0 mL, 0.263 mol) was added dropwise (ca. 30 minutes) and the solution was stirred at 115° C. for 72 h. The resulting suspension was cooled to room temperature and 150 mL water was added. The solution was extracted with dichloromethane (3×100 mL) and the organic layers combined was washed with brine (2×100 mL) and dried with MgSO4. After filtration the solvent was removed under reduced pressure to give the product as a yellow oil (Yield, 17.7 g, 44.9%). 1H NMR (400.03 MHz, CDCl3, 298 K) δ=2.20 (s, 1H, OH), 3.40 (s, 6H, OCH3), 3.55 (d, J=5.3 Hz, 2H, CHCH2), 3.63-3.61 (m, J=4.0 Hz, OCH2), 3.74-3.72 (m, J=4.0 Hz, 2H, CH2OH), 4.52 (t, 1H, CH(OCH3)2. 13C{1H} NMR (100.59 MHz, CDCl3, 298 K) δ=54.12 (2C, CH3), 61.82 (1C, CH2OH), 70.78 (1C, CHCH2O), 73.00 (1C, OCH2CH2), 102.73 (1C, CH). Anal. Calcd. for C6H14O4: C, 47.99; H, 9.40. Found C, 45.02; H, 8.74

1. stirringthe solution was stirred at 115° C. for 72 h
2. temperatureThe resulting suspension was cooled to room temperature
3. extractionThe solution was extracted with dichloromethane (3×100 mL)
4. washthe organic layers combined was washed with brine (2×100 mL)
5. dry with materialdried with MgSO4
6. filtrationAfter filtration the solvent
7. customwas removed under reduced pressure

ORD record

ord-554c97d422a34e06ab6fcd6c5b3414f8

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436104B2