Reaktion #516944

Reaktionsgleichung

sodium hydroxide

lithium

hydride

4-benzyloxybenzonitrile

→

title compound

Ausbeute 110.0%

4-Benzyloxybenzylamine

Ausbeute 110.0%

Lösungsmittel

THF

Water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to 0°
2. 2
   workup.STIRRINGwith stirring
3. 3
   FiltrationThe resulting precipitate was filtered off
4. 4
   Waschenwashed with diethyl ether (100 ml) and toluene (200 ml)
5. 5
   WaschenThe fltrate was washed with sodium chloride solution
6. 6
   Trocknendried over sodium sulphate
7. 7
   Sonstigethe solvent removed by evaporation in vacuo
8. 8
   Sonstigeto give a waxy solid

Vorschrift

To a stirred suspension of lithium alminium hydride (1.75 g, 0.46 mol) in THF (800 ml) at 0° was added 4-benzyloxybenzonitrile (43.0 g, 0.23 mol) in THF (600 ml), dropwise over 4 h. The reaction mixture was allowed to warm to room temperature and stirred for 16 h and then cooled to 0°. Water (30 ml) was added and 2M sodium hydroxide solution (80 ml) was then added dropwise with stirring. The resulting precipitate was filtered off washed with diethyl ether (100 ml) and toluene (200 ml). The fltrate was washed with sodium chloride solution, dried over sodium sulphate and the solvent removed by evaporation in vacuo, to give a waxy solid. The two soilds were combined to give the title compound (48.26 g, 110%). 1H NMR (CDCl3) δ 7.46-7.25 (5H, br m), 7.23 (2H, d, J 8.75 Hz), 6.95 (2H, d, J 8.7 Hz), 5.07 (2H, s), 3.81 (2H, s) and 1.50 (2H, br s). MS (ES) m/e 197 [M+NH4]+.

Quelle