Water → 3-(Tetradecyloxy)propan-1-ol

HRID 463644

Reaktionsgleichung

Reaktionsgleichung von HRID 463644
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[CH2:6](Br)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[K+].O>CS(C)=O.O1CCCC1>[CH2:19]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH3:6]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8208Myristyl bromideHCID 104421,3-PropanediolHCID 14797Potassium Hydroxide

Produkt 1

HCID 1142393-(Tetradecyloxy)propan-1-olAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21830753dimethylsulfoxide THFLösungsmittel

Versuchsvorschrift

In 70 ml of a mixture of dimethylsulfoxide-tetrahydrofuran (1:1) are dissolved 12.3 g of trimethylene glycol and 15 g of tetradecyl bromide. To the solution is added 12 g of powdery potassium hydroxide. The mixture is vigorously stirred for one hour at a room temperature, which is refluxed under heating for two hours. The reaction mixture is poured into 400 ml of cold water, which is neutralized and subjected to extraction with ethyl acetate, then washed with water and dried. The resultant is concentrated to dryness, and the residue is dissolved in methanol when hot. Cooling of the solution gives precipitation of crystals, which are removed by filtration. The filtrate is refined by means of chromatography employing silica-gel (eluent:chloroform) to give 5.1 g of the end-product.

Aufarbeitung

  1. temperaturewhich is refluxed
  2. temperatureunder heating for two hours
  3. extractionsubjected to extraction with ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationThe resultant is concentrated to dryness
  7. dissolutionthe residue is dissolved in methanol when hot
  8. temperatureCooling of the solution
  9. customgives
  10. customprecipitation of crystals, which
  11. customare removed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-114af40f277c494d890493369382aa3d
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04544512

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