Water → 2-Aminooctadecane-1,3-diol

HRID 1614660

Reaction equation

HRID 1614660 reaction equation
O.[OH-].[K+].[CH3:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]([OH:24])[C@@H:20]([NH2:23])[CH2:21][OH:22]>CO>[NH2:23][CH:20]([CH:19]([OH:24])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH3:4])[CH2:21][OH:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 91486Sphinganine

Product 1

HCID 31262-Aminooctadecane-1,3-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

158 g of the above compound are dissolved in 1054 cm3 of methanol including 10% of water containing 129.1 g of potassium hydroxide. The reaction medium is brought to reflux for 6 hours and then filtered through paper while hot. The filtrate is made up with 300 cm3 of water and left at 4° C. overnight. The solid formed is isolated by filtration on a glass sinter. 145 g of 2-amino-3-hydroxyoctadecanol or dihydrosphingosine are thereby obtained in pure erythro form.

Workup

  1. temperatureto reflux for 6 hours
  2. filtrationfiltered through paper while hot
  3. customThe solid formed
  4. customis isolated by filtration on a glass sinter

Sources & evidence

ORD record
ord-72b4f584634c46fab183c0ee48fed0e0
Source dataset
uspto-grants-1993_03
Patent number
US05198470

Linked notes

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