Ethylene Glycol → Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 4-cyclohexanonecarboxylic acid ethyl ester (5.00 g, 29.38 mmol) and ethylene glycol (2.13 mL, 38.19 mmol) in toluene (150 mL) was heated in a Dean-Stark trap at reflux for 1 h and was then treated with p-toluenesulfonic acid monohydrate (56.74 mg, 0.294 mmol). The reaction solution was heated an additional 30 min at reflux, cooled to 25° C., and concentrated in vacuo. The resulting oil was dissolved in ethyl acetate (200 mL), washed with water (2×50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford pure 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (6.25 g, 99.3%) as a colorless oil.

Provenance & Evidence