4-Chloro-3-nitrobenzaldehyde → 4-Chloro-3-nitrobenzyl alcohol

HRID 1674625Notes

Reaction equation

HRID 1674625 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[BH4-].[Na+]>CCO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 855054-Chloro-3-nitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 919334-Chloro-3-nitrobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-3-nitrobenzaldehyde (5.0 g, 27 mmol) in EtOH (100 mL) at rt was added portion wise NaBH4 (1.02 g, 1 eq). The mixture was stirred at RT for 2 h, concentrated in vacuo and partitioned between ether and water. The organic layer was washed with brine, dried over MgSO4 and concentrated. The title alcohol was recovered as a brownish solid (4.96 g, 98%).

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between ether and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe title alcohol was recovered as a brownish solid (4.96 g, 98%)

Sources & evidence

ORD record
ord-06219b42ac7945fa9e786bb18503fecf
Source dataset
uspto-grants-2011_08
Patent number
US08003654B2

Reaction notes

Loading…