2,6-Dinitrobenzaldehyde → (2,6-Dinitrophenyl)methanol

HRID 2226813Notes

Reaction equation

HRID 2226813 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[CH:6]=[O:7])([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[CH2:6][OH:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 690732,6-DinitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 119332(2,6-Dinitrophenyl)methanolYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2,6-dinitrobenzaldehyde (19.6 g, 0.1 mole) in methanol (200 ml), sodium borohydride (5.8 g) was added in a small portion at 15°-25° C., the resultant mixture was stirred at room temperature for 1 hour and then concentrated. To the residue, H2O (100 ml) and chloroform (100 ml) were added, followed to by stirring for 1 hour, the chloroform layer was separated, washed with H2O, dried over anhydrous MgSO4 and evaporated to afford 15.0 g of 2,6-dinitrobenzyl alcohol as yellow crystals.

Workup

  1. additionwas added in a small portion at 15°-25° C.
  2. concentrationconcentrated
  3. additionTo the residue, H2O (100 ml) and chloroform (100 ml) were added
  4. customthe chloroform layer was separated
  5. washwashed with H2O
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-224b5304348e4e62893f9c74f5d681ae
Source dataset
uspto-grants-1994_09
Patent number
US05350660

Reaction notes

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