Benzyl Bromide → HCID 3735677, compound

Participants

Reaction Conditions

Reaction Steps

A 500-ml four-necked flask equipped with a thermometer and a condenser was charged with 2.4 g of a piece of magnesium and 120 ml of absolute ether, to which a part of 17 g of benzyl bromide was added with heating. After a reaction started, the remaining amount of benzyl bromide was added dropwise to such a degree that reflux continued. After completion of the drop addition, the resultant mixture was stirred further for 1 hour at room temperature to obtain a liquid reaction mixture. A 500-ml four-necked flask equipped with a thermometer was charged with a suspension of 1 g of copper iodide in 60 ml of absolute ether, to which the liquid reaction mixture was added dropwise at -5° C. After stirring the resultant mixture for 1 hour at the same temperature, it was cooled to -20° C. A solution of 8.6 g of 2-cyclohexen-1-one in 10 ml of absolute ether was added dropwise to the mixture, and the temperature of the resulting liquid reaction mixture was then raised to room temperature while stirring for 24 hours. The liquid reaction mixture was washed with water, dried, filtered and concentrated, and 21 g of the resulting crude product were purified by column chromatography, thereby obtaining 9.6 g (yield: 57%) of 3-benzylcyclohexenone.

Provenance & Evidence