Toluene → 3,3-Dimethyl-12-isopropyl-1-aza-1,5,9-cyclododecatriene

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Reaction Steps

2.57 g (0.01 mol) of nickel acetylacetonate and 1.66 g (0.01 mol) of triethyl phosphite are dissolved in 120 g of absolute toluene under protective gas (argon), whereupon the solution is saturated at 20°-25° C. with 1,3-butadiene. There is subsequently slowly added dropwise, whilst a weak flow of 1,3-butadiene is being introduced, 3.9 g (0.03 mol) of ethoxy-diethylaluminium. The mixture is heated to 60° C. and, as a strong flow of 1,3-butadiene is being fed in, 122.5 g (0.98 mol) of N-isobutylidene-2-methylpropenylamine [produced by reaction of isobutyraldehyde with ammonia according to J. Org. Chem., 26, 1822-25 (1961)] is added dropwise, within 45 minutes, in such a manner that the introduced butadiene is exactly all used up. After completion of the dropwise addition, stirring is maintained for one further hour at 60° C., with the continuous feeding in of 1,3-butadiene, and the temperature is then lowered to 20°-25° C. The catalyst is inactivated by the addition of 0.32 g (0.01 mol) of sulfur, and the reaction solution is distilled. Subsequent fine distillation yields 212.5 g (0.912 mol) of 3,3-dimethyl-12-isopropyl-1-aza-1,5,9-cyclododecatriene; b.p. 54°-55° C./1.33 Pa; nD20 =1.4832.

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