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

HRID 982302Notes

Reaction equation

HRID 982302 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:7]=1[CH:8]=[O:9])([O-:5])=[O:4]>[OH-].[Na+].CO>[N+:3]([C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:7]=1[CH2:8][OH:9])([O-:5])=[O:4]

Participants

5

Reactant 2

HCID 690732,6-DinitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 119332(2,6-Dinitrophenyl)methanolYield 90.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.1 grams of sodium borohydride dissolved in 16 ml of 0.2N sodium hydroxide (temperature 10-23 degrees Centigrade) was dropwise added to a solution of 10 grams of 2,6-dinitrobenzaldehyde in 75 ml of methanol. The reaction mixture was stirred at room temperature for 30 minutes. The methanol was then removed under vacuum and the water residue extracted several times with ether. The ether washings were dried over anhydrous magnesium sulfate and filtered. After solvents were removed on a rotary evaporator under reduced pressure, the residue was recrystallized 3 times from a chloroform/carbon tetrachloride composition yielding 9.17 grams of 2,6-dinitrobenzyl alcohol.

Workup

  1. customThe methanol was then removed under vacuum
  2. extractionthe water residue extracted several times with ether
  3. dry with materialThe ether washings were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customAfter solvents were removed on a rotary evaporator under reduced pressure
  6. customthe residue was recrystallized 3 times from a chloroform/carbon tetrachloride composition

Sources & evidence

ORD record
ord-990d9aaad0fb4b49aeba629c729931b9
Source dataset
uspto-grants-1991_02
Patent number
US04996136

Reaction notes

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