Diisobutylaluminum hydride → 2-Chloro-4-nitrobenzyl alcohol

HRID 576954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576954
[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]

Komponenten

4

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c760b1b6c21546f5bf37cadb0614cdf4
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040538B2

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