Sulfuric Acid → 11-Amino-2,2-dimethyltridecan-1-ol
Reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH:8]=[CH:7][CH2:6][CH:5]([CH2:14][CH3:15])[N:4]=[CH:3]1.S(=O)(=O)(O)[OH:18].[H][H]>O.[Pt]>[CH3:1][C:2]([CH3:16])([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([CH2:14][CH3:15])[NH2:4])[CH2:3][OH:18]Participants
Procedure
199 g (0.91 mol) of 3,3-dimethyl-12-ethyl-1-aza-1,5,9-cyclododecatriene is 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 means of subsequent steam distillation for 20 minutes. The aqueous sulphuric acid solution is then hydrogenated under normal pressure at 20°-25° C. in the presence of a platinum/charcoal catalyst (5% by weight of platinum), with absorption of 3 mols of hydrogen, to yield 2,2-dimethyl-11-ethyl-11-aminoundecanol. After removal of the catalyst by filtration, the aqueous solution is neutralised with concentrated sodium hydroxide solution; the amino alcohol separating out is extracted with toluene, and distilled to thus obtain 149 g (0.613 mol) of 2,2-dimethyl-11-ethyl-11-aminoundecanol corresponding to a yield of 67.4% of theory; b.p. 118° C./0.05 Torr; nD20 =1.4656.
Workup
- customImpurities are removed by means of subsequent steam distillation for 20 minutes
Sources & evidence
- ORD record
- ord-a35a09d17d614c0cbf1bd30ca0145d74
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04289905
Reaction notes
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