(2-Amino-5-(trifluoromethoxy)phenyl)methanol → 2-Amino-5-(trifluoromethoxy)benzaldehyde

HRID 722342

Reaktionsgleichung

Reaktionsgleichung von HRID 722342
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH2:4][OH:5]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

4

Edukt 1

HCID 21925552(2-Amino-5-(trifluoromethoxy)phenyl)methanol

Produkt 1

HCID 218835962-Amino-5-(trifluoromethoxy)benzaldehydeAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

The 2-amino-5-trifluoromethoxybenzyl alcohol from Step 2 (9.7 g, 47 mmol) and manganese (IV) oxide (21 g, 240 mmol) were refluxed in chloroform (200 mL) for 1 hour. The contents were allowed to cool and filtered. The filtrate was concentrated in vacuo leaving an amber oil (8.2 g) which solidified. The oil was distilled (bulb to bulb apparatus) at 50° C. (0.1 mm) to afford a yellow solid (7.2 g). The solid was recrystallized from hexanes to afford the desired 2-amino-5-(trifluoromethoxy)-benzaldehyde as yellow crystals (4.4 g, 46%): mp. 42–44° C. 1H NMR (CDCl3, 300 MHz) 9.81 (s, 1H), 7.36 (s, 1H), 7.20 (d, 1H, J=9.0 Hz), 6.64 (d, 1H, J=9.0 Hz). EIHRMS m/z 205.0328 (M+, Calc'd 205.0350).

Aufarbeitung

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-85bb0dc6e24343d8832144e1fe98e397
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138411B2

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