Sodium Acetate → 7-(Oxan-2-yloxy)heptanal

HRID 329526

Reaktionsgleichung

Reaktionsgleichung von HRID 329526
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>C(Cl)Cl.C(OCC)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15]

Komponenten

6

Edukt 3

HCID 517045Sodium AcetateHCID 103984241-Heptanol, 7-[(tetrahydro-2H-pyran-2-yl)oxy]-HCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 1821847-(Oxan-2-yloxy)heptanalAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 20.37 g of 7-(tetrahydropyran-2-yloxy)-1-heptanol in 200 ml of methylene chloride was added, whilst ice-cooling, to a mixture of 40.60 g of pyridinium chlorochromate, 3.86 g of sodium acetate and 200 ml of methylene chloride. The resulting mixture was stirred at 0° C. for 1 hour and then at room temperature for 3 hours, after which was diluted with 1.5 liter of diethyl ether and passed through a column containing 250 g of silica gel. The eluate was concentrated by evaporation under reduced pressure, and the residue was subjected to column chromatography through 400 g of silica gel. 14.11 g of 7-(tetrahydropyran-2-yloxy)heptanal were obtained, as a colorless oil, from those fractions eluted with mixtures of hexane and ethyl acetate ranging from 40:1 to 9:1 by volume.

Aufarbeitung

  1. waitat room temperature for 3 hours
  2. additioncontaining 250 g of silica gel
  3. concentrationThe eluate was concentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2cc8ed167f28461a83227f6f1003278d
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891363

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