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

HRID 129376Notes

Reaction equation

HRID 129376 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 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, m.p. 92.5°-93.5° C.

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-698957f69e024b299aa33cefabccd756
Source dataset
uspto-grants-1995_11
Patent number
US05468589

Reaction notes

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