2,4-Dinitrobenzaldehyde → 2,4-Dinitrobenzenemethanol

HRID 1903418Notes

Reaction equation

HRID 1903418 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])([O-:5])=[O:4]>C(O)C>[N+:3]([C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=1[CH2:8][OH:9])([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 682502,4-DinitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 209742,4-DinitrobenzenemethanolYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium borohydride (0.2 g, 10 mmol) in ethanol (40 ml) was added dropwise to 2,4-dinitrobenzaldehyde (1.96 g, 10 mmol) in ethanol (40 ml) and stirred for 1 h. The reaction mixture was then evaporated in vacuo, partitioned between ether and aqueous sodium bicarbonate, the ether layer dried (magnesium sulphate) and evaporated in vacuo to yield 2,4-dinitrobenzyl alcohol as a brown solid (1.147 g, 58%), m.p. 105°-110° C.;

Workup

  1. customThe reaction mixture was then evaporated in vacuo
  2. custompartitioned between ether and aqueous sodium bicarbonate
  3. dry with materialthe ether layer dried (magnesium sulphate)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-463f7805ed2c4534ad9d46b892cebb62
Source dataset
uspto-grants-1984_03
Patent number
US04436751

Reaction notes

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