Acetonitrile → HCID 178516167, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of silver nitrate (17.5 g, 0.104 moles) dissolved in 100 ml water, 50 g (0.209 moles) trans-4-(4-chlorophenyl)cyclohexane carboxylic acid was added. To this solution acetonitrile (250 ml) was added and under stirring and heated to reflux. 33.1 g (0.209 moles) 1,4-naphthoquinone was then added. 120 g (0.525 mole) ammonium persulfate dissolved in 400 ml water was added drop-wise to the stirred solution and continued reflux for 2 hours. The reaction solution was then cooled to 0-5° C. and extracted with methylene chloride. The organic layer was first washed with water, followed by 10% sodium carbonate aqueous solution, and further with water until the pH is neutral. The organic layer was distilled to eliminate methylene chloride and was then stirred in acetonitrile and filtered. The solid obtained was crystallized from acetonitrile to obtain 15 g of trans-2-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthoquinone (20% yield). M.P. 146-149 (uncorrected), 1H NMR (400 MHz), δH (d6-CDCl3) 8.07-8.14 (2H, m, Naphth), 7.65-7.74 (2H, m, Naphth), 7.27-7.30 (2H, d, arom.), 7.07-7.19 (2H, d, arom.), 6.80 (1H, s, naphtho.), 2.98-3.01 (1H, tt, CH), 2.54-2.58 (1H, tt, CH—), 1.25-2.03 (8H, multi, CH2).

Provenance & Evidence