2-(Hydroxymethyl)-4-iodophenol → 5-Iodosalicylaldehyde

HRID 722289

Reaktionsgleichung

Reaktionsgleichung von HRID 722289
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5]>CC(C)=O.[O-2].[Mn+4].[O-2]>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

4

Edukt 1

HCID 125452592-(Hydroxymethyl)-4-iodophenol

Produkt 1

HCID 2526125-IodosalicylaldehydeAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-hydroxy-5-iodobenzyl alcohol (43.5 g, 174.0 mmol) in acetone (700 mL) was added 85% activated manganese(IV) oxide (5 micron, 50 g, 494.0 mmol) and the solution stirred at room temperature for 16 hours. The manganese oxide was removed by filtration through diatomaceous earth and the filtrate concentrated in vacuo. The product was purified by flash silica chromatography (0–20% ethyl acetate in hexanes) The 2-hydroxy-5-iodobenzaldehyde was obtained as a greenish-yellow solid (24.3 g, 58%). A small amount of the 2-hydroxy-5-iodobenzaldehyde was recrystallized from methanol/water to afford an analytical sample and the remainder of the compound was used without further purification: mp 99–101° C. 1H NMR (CDCl3/300 MHz) 9.83 (s, 1H), 7.79 (d, 1H, J=2.2 Hz), 7.77 (dd, 1H, J=8.7 Hz, J=2.2 Hz), 6.81 (d, 1H, J=8.7 Hz). ESHRMS 246.9229 (M−H Calc'd 246.9256).

Aufarbeitung

  1. customThe manganese oxide was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe product was purified by flash silica chromatography (0–20% ethyl acetate in hexanes) The 2-hydroxy-5-iodobenzaldehyde

Quellen und Nachweise

ORD-Eintrag
ord-bba639585cdc46459e309ca40d5ea179
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138411B2

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