Diisobutylaluminum hydride → 2-Chloro-4-nitrobenzyl alcohol

HRID 629995ノート

反応式

HRID 629995 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].CC(C)C[AlH]CC(C)C>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 83343Methyl 2-chloro-4-nitrobenzoate

生成物 1

HCID 1041472-Chloro-4-nitrobenzyl alcohol収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

In a 250 mL round bottom flask, methyl 2-chloro-4-nitrobenzoate (5 g, 23 mmol) was dissolved in anhydrous dichloromethane (100 mL). The solution was cooled to −78° C. under nitrogen. Bis(2-methylpropyl)alumane (35 mL, 35 mmol, 1 M in hexane) was added dropwise. The mixture was stirred at −78° C. for 4 hours and quenched by addition of water (5 mL). The resulting mixture was warmed up to room temperature in 20 minutes. Na2SO4 (15 g) was added. After 10 minutes, the mixture was filtered. The filtrate was evaporated to provide (2-chloro-4-nitrophenyl)methanol (95% yield).

後処理

  1. customquenched by addition of water (5 mL)
  2. temperatureThe resulting mixture was warmed up to room temperature in 20 minutes
  3. additionNa2SO4 (15 g) was added
  4. waitAfter 10 minutes
  5. filtrationthe mixture was filtered
  6. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-778933207f774c21a42bdeb5159815dd
出典データセット
uspto-grants-2016_04
特許番号
US09315521B2

反応ノート

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