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

Participants

Reaction Steps

A mixture of ethyl levulinate (58.35 g, 400.0 mmol), ethylene glycol (75.36 g, 1.21 mol), pyridinium p-toluenesulfonate (100 mg) and toluene (200 mL) was heated at reflux under a Dean Stark trap. The trap was emptied every 15 minutes during the reaction until approximately 200 mL of reaction volatiles had been removed. The remaining toluene was removed under reduced pressure, and the resulting oil was partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer was separated and washed sequentially with water (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), and brine (50 mL); dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 68.9 g of ethyl 3-(2-methyl-1,3-dioxolan-2-yl)propanoate as a light yellow oil.

Provenance & Evidence