Ethylene Glycol → Methyl 1,4-dioxaspiro[4.5]decane-6-carboxylate

Participants

Reaction Steps

A mixture of methyl-2-oxocyclohexanecarboxylate (4-1) (7.0 g, 44.8 mmol), ethylene glycol (3.00 mL, 53.8 mmol) and p-toluenesulfonic acid monohydrate (0.853 g, 4.48 mmol) in Benzene (45 mL) was heated to reflux overnight. The reaction was then cooled to rt and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.86-3.99 (m, 4H), 3.69 (s, 3H), 2.69 (dd, 1H, J=4.9 Hz, 9.0 Hz), 1.82-1.97 (m, 3H), 1.58-1.73 (m, 3H), 1.45-1.53 (m, 1H), 1.26-1.37 (m, 1H).

Provenance & Evidence