Sodium Hydroxide → 4-Benzyloxybenzylamine

HRID 429762

反応式

HRID 429762 の反応式
[Li].[H-].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.O>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:17][CH:18]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 5613714-BenzyloxybenzonitrileHCID 3028194Lithium

生成物 1

HCID 42928454-Benzyloxybenzylamine収率 110%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

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]+.

後処理

  1. temperaturecooled to 0°
  2. stirringwith stirring
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with diethyl ether (100 ml) and toluene (200 ml)
  5. washThe fltrate was washed with sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customthe solvent removed by evaporation in vacuo
  8. customto give a waxy solid

出典と根拠

ORDレコード
ord-3a9855eb3d204946b452dc3be19d9999
出典データセット
uspto-grants-2001_11
特許番号
US06319922B1

関連ノート

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