反応 #516944

反応方程式

sodium hydroxide

lithium

hydride

4-benzyloxybenzonitrile

→

title compound

収率 110.0%

4-Benzyloxybenzylamine

収率 110.0%

溶媒

THF

Water

THF

反応条件

後処理

1. 1
   温度cooled to 0°
2. 2
   workup.STIRRINGwith stirring
3. 3
   ろ過The resulting precipitate was filtered off
4. 4
   洗浄washed with diethyl ether (100 ml) and toluene (200 ml)
5. 5
   洗浄The fltrate was washed with sodium chloride solution
6. 6
   乾燥dried over sodium sulphate
7. 7
   その他the solvent removed by evaporation in vacuo
8. 8
   その他to give a waxy solid

実験手順

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]+.

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