Sulfuric Acid → HCID 14100447, compound

Participants

Reaction Conditions

Reaction Steps

3 g. of a mixture of 96-98% sulphuric acid and oleum (1:1 w/w) cooled to 3° C. are added dropwise to the dry diisopropyl 2,2,15,15-tetrachlorohexadecane-1,16-dioate. The mixture is stirred for 10 minutes at 3° C., a colour change to orange thereby taking place. A further 2 g. of the acid mixture are added dropwise until the ester has completely dissolved and then stirred for 15 minutes at 3° C. The solution is cooled to -78° C. and a mixture of ice/dichloromethane added thereto. The frozen mixture is dissolved by slowly warming to ambient temperature while stirring with a porcelain spatula, the solution thereby becoming colourless. After separation of the phases, the aqueous phase is extracted with dichloromethane and the combined organic extracts are dried over anhydrous sodium sulphate. After removal of the solvent, there are obtained 150 mg. (yield 90% of theory) of a colourless solid; m.p. 113.5°-114.5° C., after recrystallisation from cyclohexane.

Provenance & Evidence