Ethylene Glycol → HCID 57485780, compound

Participants

Reaction Steps

A solution of 5-oxocyclohexane-1,3-dicarboxylic acid dimethyl ester (22.8 g, 106.4 mmol), ethylene glycol (13.3 g, 215 mmol) and p-toluenesulfonic acid monohydrate (0.22 g, 1.3 mmol) in toluene (230 mL), in a flask fitted with Dean-Stark trap was heated under reflux for 5 h. The reaction was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate. Organic layer was separated, washed with NaHCO3 solution and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give an oil, which was triturated with hexane and left in the fridge overnight. The precipitated solid was filtered and dried under vacuum to provide 17.1 (63%) g of the title compound, 1,4-Dioxa-spiro[4.5]decane-7,9-dicarboxylic acid dimethyl ester as a white solid. 1HNMR (400 MHz, CDCl3), δ: 3.95 (m, 4H), 3.7 (s, 6H), 2.72-2.62 (m, 3H), 2.32-2.22 (m, 1H), 2.02-1.96 (m, 2H), 1.6-1.4 (m, 3H).

Provenance & Evidence