1,3-Propanediol → 1-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

HRID 28300

Reaktionsgleichung

Reaktionsgleichung von HRID 28300
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:21][CH2:22][CH2:23][CH2:24]O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:20][CH2:24][CH2:23][CH2:22][OH:21])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

6

Edukt 3

HCID 104421,3-PropanediolHCID 10868DicyclohexylcarbodiimideHCID 5280933Gamma-Linolenic acid

Produkt 1

HCID 103371121-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of z,z,z-octadeca-6,9,12-trienoic acid (150 g) in methylene chloride (500 ml) was added dropwise to a mixture of 1,3-dihydroxypropane (205 g), 1,3-dicyclohexylcarbodiimide (130 g) and 4-(N,N-dimethylamino)pyridine (87 g) in methylene chloride (2500 ml) at room temperature under nitrogen. When tlc indicated that the reaction had gone to completion the reaction mixture was filtered. The filtrate was washed with dilute hydrochloric acid, water and saturated sodium chloride solution. The solution was dried, concentrated and purified by dry column chromatography to yield 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane as a pale yellow oil.

Aufarbeitung

  1. filtrationwas filtered
  2. washThe filtrate was washed with dilute hydrochloric acid, water and saturated sodium chloride solution
  3. customThe solution was dried
  4. concentrationconcentrated
  5. custompurified
  6. customby dry column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7ed41bb16c2a4dd79c39735e81f3521a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
USRE040480E1

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