Hydrochloric Acid → 2-Aminooctadecane-1,3,4-triol--hydrogen chloride (1/1)

HRID 1604752Notes

Reaction equation

HRID 1604752 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O[N:8]=[C:9]([C:14](=[O:34])[CH:15]([O:30]C(=O)C)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:10](OC)=[O:11].[ClH:35]>O1CCCC1>[ClH:35].[NH2:8][CH:9]([CH:14]([OH:34])[CH:15]([OH:30])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 178443136HCID 178443136, compound

Product 1

HCID 193476832-Aminooctadecane-1,3,4-triol--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

0.275 mol of lithium aluminum hydride was introduced, under argon, with continual stirring, into tetrahydrofuran. The solution was then cooled to a temperature of 0° C., and 0.055 mol of methyl 2-hydroxyimino-3-oxo-4-acetoxyoctadecanoate was slowly added. The reaction mixture was then gradually heated to 60° C. At the end of the reaction, marked by the disappearance of the starting materials, the reaction mixture was hydrolysed while cold with a hydrochloric acid solution. A precipitate formed, which was filtered off, and then the solvent was evaporated under vacuum. After crystallizing from a mixture of ethyl ether and acetonitrile, a white solid was obtained which, filtered and dried, gave 14.2 g of 2-aminooctadecane-1,3,4-triol hydrochloride in the form of a white powder.

Workup

  1. additionwas slowly added
  2. customAt the end of the reaction
  3. customA precipitate formed
  4. filtrationwhich was filtered off
  5. customthe solvent was evaporated under vacuum
  6. customAfter crystallizing from a mixture of ethyl ether and acetonitrile
  7. customa white solid was obtained which
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-b199fd8cc7d24a76a79a2435d6404f1e
Source dataset
uspto-grants-1999_11
Patent number
US05994586

Reaction notes

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