Hydrochloric Acid → 2-[2-(3-Cyanopropyl)benzyl]-1,3-cyclohexanedione

Participants

Reaction Conditions

Reaction Steps

A mixture of 22 g (0.079 mol) of 2-[2-(3-chloropropyl)benzyl]-1,3 -cyclohexanedione 3 and 15.5 g (0.316 mol) of NaCN in 250 ml of dry dimethyl sulfoxide was stirred at 95° C for 3 hours. The reaction was filtered while hot to remove NaCl, and the dimethyl sulfoxide was distilled out under high vacuum. The residue was dissolved in 400 ml H2O, filtered through a diatomaceous earth filter aid (celite) to give a red solution and neutralized by the rapid addition of 40 ml concentrated HCl. The precipitate was recrystallized twice from ethyl acetate to give 16 g of the cyanodione, IIa, mp 143° C.

Provenance & Evidence