Ethylene Glycol → 2-Methyl-2-(3-butenyl)-1,3-dioxolane

Participants

Reaction Steps

In a 200 mL RB flask, 5-hexen-2-one (37.18 g, 0.3788 mol) was mixed with ethylene glycol (23.49 g, 0.3788 mol), 0.72 g p-toluenesulfonic acid monohydrate and 40 mL toluene. A graduated water collector and a reflux condenser were connected to the flask. The mixture was refluxed overnight. The reaction was completed as shown by the amount of water collected (ca. 7 mL). After evaporation of toluene, the mixture was distilled under reduced pressure to gave 25 g of pure product. 1H NMR(CDCl3): δ1.31(s, 3H, —CH3); 1.72(m, 2H, CH2═CHCH2CH2—); 2.13(m, 2H, CH2═CHCH2CH2—); 3.92(m, 4H, —OCH2CH2O—); 4.95(m, 2H, CH2═CH—); 5.80(m, 1H, CH2═CH—).

Provenance & Evidence