Reaktion #587610

Reaktionsgleichung

2-methoxy-5-nitrobenzylalcohol

SnCl2.H2O

NaOH

→

aniline 3-hydroxymethyl-4-methoxyaniline

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Extraktionextracted with ether
3. 3
   WaschenThe organic layer was washed with water
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated under vacuum

Vorschrift

A mixture of 2-methoxy-5-nitrobenzylalcohol (1.02 g, 6.03 mmol) and SnCl2.H2O (6.8 g, 30.15 mmol) in EtOH (20 mL) was heated at 70° C. for 1 hour. After cooling, the mixture was treated with 2M NaOH and extracted with ether. The organic layer was washed with water, dried, and evaporated under vacuum to provide 2.18 g (84%) of the aniline 3-hydroxymethyl-4-methoxyaniline: 1H NMR (DMSO-d6, 500 MHz) δ 6.66 (d, 1H, J=2.2 Hz), 6.61 (d, 1H, J=8.6 Hz), 6.38 (dd, 1H, J=2.4 and 8.2 Hz), 4.81 (t, 1H, J=5.5 Hz), 4.54 (br, 2H), 4.37 (d, 2H, J=5.8 Hz), 3.61 (s, 3H).

Quelle