Sulfuric Acid → 11-Amino-2,2-dimethyltridecan-1-ol

Participants

Reaction Steps

199 g (0.91 mol) of the 3,3-dimethyl-12-ethyl-1-aza-1,5,9-cyclododecatriene prepared according to Example 7 are added dropwise in the course of 15 minutes to a solution of 150 g (1.53 mols) of sulphuric acid in one liter of water. Impurities are removed by a subsequent 20 minute stream distillation. The aqueous sulphuric acid solution is then hydrogenated at normal pressure and 20°-25° C. in the presence of a platinum-on-charcoal catalyst (5% by weight of platinum) with the absorption of 3 mols of hydrogen, to give 2,2-dimethyl-11-ethyl-11-aminoundecanol. After filtering off the catalyst, the aqueous solution is neutralised with concentrated sodium hydroxide solution and the amino-alcohol which separates out is extracted by shaking with toluene and distilled. 149 g (0.613 mol) of 2,2-dimethyl-11-ethyl-11-aminoundecanol are obtained, corresponding to a yield of 67.4% of theory; boiling point 118° C./0.05 mm Hg; nD20 =1.4656.

Provenance & Evidence