Diethyl Ether → (1-Ethylcyclohexyl)acetaldehyde

Participants

Reaction Steps

After adding iodobenzene diacetate (1.61 g, 4.98 mmol) to a solution of 2-(1-ethylcyclohexyl)ethanol (708 mg, 4.53 mmol) in methylene chloride (15 mL) at room temperature, 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (70.8 mg, 0.450 mmol) was added and the mixture was stirred for 15 hours. Diethyl ether was added to the reaction mixture, which was then washed with 10% aqueous sodium thiosulfate, 1N hydrochloric acid and saturated aqueous sodium hydrogencarbonate in that order. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound as an orange oil (1.54 g).

Provenance & Evidence