3-Nitrobenzaldehyde → 3-Nitrobenzyl alcohol

HRID 547585

Reaction equation

HRID 547585 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 692673-Nitrobenzyl alcoholYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-nitrobenzaldehyde (1) (200 g, 1.32 mol) in methanol (1000 mL) at 0° C. under N2 atmosphere was slowly added NaBH4 (25 g, 0.66 mol) and then the reaction mixture was allowed to stir at room temperature for 1 h. The reaction mixture was re-cooled to 0° C. and quenched with ice-water, methanol was removed under reduced pressure and the residue was extracted with CH2Cl2 (5×200 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to furnish compound 2 (190.7 g, 93%) as liquid which was taken as such for next step.

Workup

  1. customat 0° C.
  2. temperatureThe reaction mixture was re-cooled to 0° C.
  3. customquenched with ice-water, methanol
  4. customwas removed under reduced pressure
  5. extractionthe residue was extracted with CH2Cl2 (5×200 mL)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c623c18fdc7a4d80828cab76ff0e972e
Source dataset
uspto-grants-2011_05
Patent number
US07939556B2

Linked notes

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