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Toluene → HCID 22841014, Verbindung

HRID 414778
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 414778
[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:15]([OH:16])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[OH-].[K+].C1(C)C=CC=CC=1>O>[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:15]([O:16][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 22841016HCID 22841016, Verbindung

Produkt 1

HCID 22841014HCID 22841014, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 1.037 g of dl-cis-2-benzyloxymethyl-3-hydroxytetrahydropyran (prepared as described in Preparation 9), 1.709 g of hexadecyl bromide, 0.77 g of potassium hydroxide and 15 ml of toluene was heated, with stirring, at 120° C. for 10 hours. The reaction mixture was cooled and then poured into water. The water layer was extracted twice with diethyl ether. The organic layer and the extracts were combined, washed with water, dried and condensed by evaporation under reduced pressure. The resulting oily residue, 3.3 g, was subjected to column chromatography through 50 g of silica gel. The fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane gave 1.455 g of the title compound as a colorless oily substance.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. extractionThe water layer was extracted twice with diethyl ether
  4. washwashed with water
  5. customdried
  6. customcondensed
  7. customby evaporation under reduced pressure
  8. washThe fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-06ca8ad9268c4c45a2f4b81c14c5ba6c
Quelldatensatz
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04794183

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