Reaktion #1276685

Reaktionsgleichung

product

1-(4-pentafluoroethyloxy-phenyl)-3-p-tolyl-1H-[1,2,4]triazole

KOH

→

aldehyde

Ausbeute 30.7%

4-[1-(4-pentafluoro ethyloxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzaldehyde

Ausbeute 30.7%

Lösungsmittel

water

dioxane

acetonitrile

water

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added in portions over 10 min
2. 2
   TemperaturThe solution was then heated
3. 3
   Temperaturto reflux for 4 h
4. 4
   Temperaturcooled
5. 5
   ExtraktionThe solution was extracted with ether (2×200 mL)
6. 6
   Sonstigethe combined organic layer was dried
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto give an orange oil
9. 9
   TemperaturThe solution was heated
10. 10
    Temperaturto reflux for 2 h
11. 11
    Temperaturcooled
12. 12
    SonstigeThe aldehyde precipitated
13. 13
    Filtrationwas collected by filtration
14. 14
    SonstigeRecrystallization from MeOH/H2O

Vorschrift

The product from Step 1 (7.0 g, 18.7 mmol) was dissolved in acetonitrile (200 mL) and stirred at ambient temperature while ceric ammonium nitrate (32 g, 58 mmol) in water (60 mL) was added in portions over 10 min. The solution was then heated to reflux for 4 h, cooled, and diluted with water (200 mL). The solution was extracted with ether (2×200 mL), and the combined organic layer was dried and concentrated to give an orange oil. This material was dissolved in dioxane (40 mL) and treated with a solution of KOH (5 g, 90 mmol) in water (20 mL). The solution was heated to reflux for 2 h, then cooled and diluted with water (100 mL). The aldehyde precipitated and was collected by filtration. Recrystallization from MeOH/H2O gave the pure aldehyde as a white solid (2.2 g, 30%): mp 137-144° C. 1H NMR (300 MHz, CDCl3) δ 10.1 (s, 1H), 8.65 (s, 1H), 8.40 (d, J=8.4 Hz, 2H), 8.0 (d, J=8.4 Hz, 2H), 7.85 (d, J=9 Hz, 2H), 7.45 (d, J=9 Hz, 2H); ESIMS m/z 384.2 (M+H).

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