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

HRID 1577941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1577941
[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]

Komponenten

6

Edukt 3

HCID 1118Sulfuric Acid2×HCID 537432543,3-Dimethyl-12-ethyl-1-aza-1,5,9-cyclododecatrieneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1294176211-Amino-2,2-dimethyltridecan-1-olAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customImpurities are removed by means of subsequent steam distillation for 20 minutes

Quellen und Nachweise

ORD-Eintrag
ord-a35a09d17d614c0cbf1bd30ca0145d74
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04289905

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