Reaktion #57925

Reaktionsgleichung

4-{2-[1-(4-tert-butyl-phenyl)-ethylideneaminooxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester

sodium hydroxide

→

title compound

Ausbeute 47.0%

4-{2-[({(E)-1-[4-(tert-Butyl)-phenyl]-ethylidene}amino)oxy]-ethoxy}-2-hydroxy-benzoic Acid

Ausbeute 47.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was heated
2. 2
   Temperaturat reflux for 40 minutes
3. 3
   Einengenit was concentrated to a small volume
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   TrocknenThe combined organics were dried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by flash chromatography

Vorschrift

To a solution of 4-{2-[1-(4-tert-butyl-phenyl)-ethylideneaminooxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester (0.546 g, 1.29 mmol) in ethanol (10 mL) was added 1 M sodium hydroxide solution (2 mL, 2 mmol) and the reaction was heated at reflux for 40 minutes. After cooling to room temperature, it was concentrated to a small volume, acidified to pH 1 with 2M hydrochloric acid solution and extracted with ethyl acetate. The combined organics were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (30/70)+1% formic acid to afford the title compound (0.224 g, 47%) as a white solid. mp=157.4-158.7° C.; mass spectrum (+ESI, M+H) m/z 372. 1H NMR (400 MHz, DMSO-d6); δ 13.60 (bs, 1H), 11.50 (bs, 1H), 7.67 (d, 1H), 7.57 (d, 2H), 7.40 (d, 2H), 6.52 (m, 2H), 4.40 (t, 2H), 4.30 (t, 2H), 2.13 (s, 3H), 1.27 (s, 9H). Elemental analysis: Calcd. for C21H25NO5: C, 67.91; H, 6.78; N, 3.77, Found: C, 67.69; H, 6.81; N, 3.68.

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