2-Chloro-1,4-naphthoquinone → HCID 20437477, compound

Participants

Reaction Steps

A mixture of 2-chloro-1,4-naphthoquinone (21 g), 4-t-butylcyclohexane-1-carboxylic acid (19.8 g) and silver nitrate (3.6 g) was heated at 70°-75° C. with vigorous stirring in a solvent mixture of acetonitrile (30 ml), sulpholane (90 ml) and water (210 ml) whilst a solution of ammonium persulphate (34.2 g) in water (60 ml) was added dropwise during 30 minutes. Stirring and heating was continued for a further hour, the mixture cooled in ice and extracted with diethyl ether. The extracts were washed with aqueous sodium bicarbonate solution, dried and evaporated under reduced pressure to a semi-solid which was crystallised twice from acetonitrile to provide 2-(4-butylcyclohexyl)-3-chloro-1,4-naphthoquinone m.p. 107°-110°.

Provenance & Evidence