Iodine → HCID 178442143, compound

Participants

Reaction Steps

14.0 g of trans-4-(4-n-pentylphenyl)-1-(4-acetylphenyl)-cyclohexane are heated for 2 hours on a steambath, together with 30 g of iodine and 100 ml of pyridine. After the evaporation of the pyridine under reduced pressure, the residue is dissolved in chloroform and purified over a short silica gel column. The eluate is evaporated and the 4-[trans-4-(4-n-pentylphenyl)-cyclohexyl]-benzoic acid remaining behind is brought to the boil for 2.5 hours with 30 ml of thionyl chloride. After distilling off the excess thionyl chloride, the 4-[trans-4-(4-n-pentylphenyl)-cyclohexyl]-benzoyl chloride is dissolved in 250 ml of dioxane and this solution mixed with 100 ml of 25% aqueous ammonia solution. The reaction mixture is poured into 1.5 liters of ice water and the precipitated 4-[trans-4-(4-n-pentylphenyl)-cyclohexyl]-benzamide filtered off and dried. The dry amide is dissolved at 40° in 170 ml of dimethyl formamide. To this solution are added dropwise at 50° , in the course of 30 minutes, 26 g of phosphorus oxide trichloride. After 1 hour the reaction mixture is poured into 300 ml of icewater. After extracting several times with 100 ml amounts of dichloromethane, washing of the extracts with 5% sodium bicarbonate solution and then with water, drying over sodium sulphate and evaporation, there is obtained trans-4-(4-n-pentylphenyl)-1-(4-cyanophenyl)-cyclohexane which is purified by recrystallisation from ethanol; m.p. 80°, c.p. 160°.

Provenance & Evidence