1,2,3,6-Tetrahydrophthalimide → 2-Octadecanoyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

A solution of 4-cyclohexene-1,2-dicarboximide (151g) and triethylamine (300 mls) in dichloropropane (900 mls) was maintained at a temperature of 50° C during the addition thereto over a period of 10 minutes, with constant stirring, of a solution of stearoyl chloride (302.5g) in a dichloropropane (300 mls). The mixture was stirred at 50° C for a further period of 10 minutes during which time triethylamine hydrochloride precipitated out, and was then filtered hot. The filtered precipitate was then washed with small portions of hot dichloropropane and the washings were combined with the filtrate. The solvent from the combined washings and filtrate was then evaporated off in a rotary evaporator to yield solid N-stearoyl-4-cyclohexene-1,2-dicarboximide, which was recrystallised from 60° - 80° petroleum ether.

Provenance & Evidence