Ethylene Glycol → Ethyl 2-methyl-1,3-dioxolane-2-propionate

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Reaction Steps

In a flask equipped by a Dean-Stark trap, a mixture of ethyl levulinate (28.83 g; 200 mmol), ethylene glycol (37.24 g; 600 mmol) and a catalytic amount of pyridinium para-toluenesulfonic acid in toluene (200 mL) was heated at reflux until the theoretical amount of water was distilled off. After cooling, the mixture was washed with a saturated solution of sodium hydrogen carbonate. The basic layer was extracted with diethylether and the organics were combined, then washed with brine and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford the ethyl 3-(2-methyl-1,3-dioxolan-2-yl)propanoate as a colorless oil. ESI/APCI(+): 189 (M+H). 1H NMR (CDCl3): δ 4.12 (q, J=7.14 and 14.25 Hz, 2H, CO2CH2CH3); 3.93 (m, 4H, OCH2CH2O); 2.37 (m, 2H, CH2); 2.02 (m, 2H, CH2); 1.32 (s, 3H, CH3); 1.25 (t, J=7.14 Hz, 3H, CO2CH2CH3).

Provenance & Evidence