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

HRID 2057873Notes

Reaction equation

HRID 2057873 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

6

Reactant 3

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

Product 1

HCID 1294176211-Amino-2,2-dimethyltridecan-1-ol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  1. customImpurities are removed by a subsequent 20 minute
  2. distillationstream distillation

Sources & evidence

ORD record
ord-833ea876fef544618cb33b25b06a5b4c
Source dataset
uspto-grants-1980_07
Patent number
US04213901

Reaction notes

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