2-Iodobenzylic alcohol → 2-Iodobenzaldehyde

HRID 420418

Reaktionsgleichung

Reaktionsgleichung von HRID 420418
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[I:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][OH:16]>ClCCl.CCOCC>[I:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16]

Komponenten

5

Edukt 2

HCID 1076292-Iodobenzylic alcoholHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 6434392-IodobenzaldehydeAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of pyridinium chlorochromate (8.28 g, 38.4 mmol) and dry celite (5.00 g) in dry dichloromethane was stirred at room temperature for 15 min. 2-Iodobenzyl alcohol (3.03 g, 12.9 mmol) in dry dichloromethane (50 ml) was added. The suspension was shielded from light and stirred at room temperature for 2 h after which it was diluted with ether, and filtered through celite. The cloudy brown filtrate was concentrated to a red-brown gummy solid which was dissolved in dichloromethane and passed through a short silica column, eluting with dichloromethane. The solution was concentrated to give 2-iodobenzaldehyde (19) as a pale yellow oil (2.87 g, 95%).

Aufarbeitung

  1. dry with materialdry celite (5.00 g) in dry dichloromethane
  2. stirringstirred at room temperature for 2 h after which it
  3. filtrationfiltered through celite
  4. concentrationThe cloudy brown filtrate was concentrated to a red-brown gummy solid which
  5. dissolutionwas dissolved in dichloromethane
  6. washeluting with dichloromethane
  7. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1f5a88fde8d14cf491d019b6f642a41b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097238B2

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