Diethyl Ether → 3-Butylcyclohexanone

Participants

Reaction Steps

To 20 ml of anhydrous diethyl ether was added 1.9 g (10 mmol) of cuprous iodide, and at -78° C in an atmosphere of nitrogen, 12.8 ml (20 mmol) of a 15 % by weight hexane solution of n-butyllithium was added. The mixture was stirred for 30 minutes, and then, 960 mg (10 mmol) of 2-cyclohexenone was added. The mixture was further stirred for one hour. Then, 3.93 g (50 mmol) of acetyl chloride was added, and the mixture was stirred for 2 hours at room temperature. After the reaction, the reaction product was post-treated, extracted, washed, and dried in the same way as in Example 4 to afford 2.662 g of a crude product. The crude product was purified by column chromatography (silica gel) to afford 56 mg (0.4 mmol) of 3-n-butylcyclohexanone as a by-product in a yield of 4% and 1.103 g (5.6 mmol) of 2-acetyl-3-n-butylcyclohexanone as a main product in a yield of 56%.

Provenance & Evidence