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

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Reaction Conditions

Reaction Steps

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{H} 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

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