Diisobutylaluminum hydride → 2-Chloro-4-nitrobenzyl alcohol
Reaction equation
[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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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).
Workup
- customquenched by addition of water (5 mL)
- temperatureThe resulting mixture was warmed up to room temperature in 20 minutes
- additionNa2SO4 (15 g) was added
- waitAfter 10 minutes
- filtrationthe mixture was filtered
- customThe filtrate was evaporated
Sources & evidence
- ORD record
- ord-c760b1b6c21546f5bf37cadb0614cdf4
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040538B2
Reaction notes
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