1-Bromooctadecane → Dibutyl distearylmalonate

Participants

Reaction Steps

62 m mol of dibutyl malonate, 63 m mol of stearyl bromide, and 69 m mol of sodium were made to react in butanol in the presence of 2 m mol of a crown ether, thereby forming 30 m mol of dibutyl distearylmalonate. Dibutyl distearylmalonate, 15 m mol, was first hydrolyzed, and was then heated in vacuum to be decarboxylated, whereby obtaining 10 m mol of 2-octadecyl eicosanoic acid. This acid, 8 m mol, was converted into its acid chloride. The acid chloride was allowed to react with 10 m mol of p-amino-methlylsulfonylanilide in pyridine, thereby obtaining 7 m mol of p-methylsulfonamide-3-heptadecyleicosanoylanilide. The eicosanoylanilide, 5 m mol, was allowed to react with lead tetraacetate in toluene, thus forming 3.2 m mol of N-(2-octadecyleicosanoyl)-N'methylsulfonyl-p-quinonediimine which is represented by the following formula: ##STR29##

Provenance & Evidence