Sodium borohydride → 4,4,4-Trinitro-1-butanol

HRID 1199506Notes

Reaction equation

HRID 1199506 reaction equation
[N+:1]([C:4]([N+:12]([O-:14])=[O:13])([N+:9]([O-:11])=[O:10])[CH2:5][CH2:6][CH:7]=[O:8])([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]([N+:9]([O-:11])=[O:10])([N+:12]([O-:14])=[O:13])[CH2:5][CH2:6][CH2:7][OH:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 144017654,4,4-Trinitrobutyraldehyde

Product 1

HCID 138979744,4,4-Trinitro-1-butanolYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 4,4,4-trinitrobutaldehyde (878 g, 4.24 mol) was dissolved in methanol (1000 ml) and cooled in an ice bath while NaBH4 (130.7 g, 3.44 mol) was added portion-wise. The mixture was stirred at room temperature overnight under a nitrogen purge which removed much of the solvent. The thick suspension was hydrolyzed with 6 N HCl (approx. 41) and the product extracted with CH2Cl2 (3×1000 ml). The extracts were washed with water (1000 ml), saturated NaHCO3 (2×1000 ml), and water (1000 ml). The product solution was dried over anhydrous MgSO4 and concentrated to yield 554 g (63%) of a yellow oil, nD =4735 (19C). The infrared spectrum showed peaks at 3619, 3370, 2950, 2890, 1595, 1305, 1058 and 801 cm-1.

Workup

  1. additionwas added portion-wise
  2. custompurge which
  3. customremoved much of the solvent
  4. extractionthe product extracted with CH2Cl2 (3×1000 ml)
  5. washThe extracts were washed with water (1000 ml), saturated NaHCO3 (2×1000 ml), and water (1000 ml)
  6. dry with materialThe product solution was dried over anhydrous MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8843dd21a68142fd9fa58bbd372c5a7b
Source dataset
uspto-grants-1990_02
Patent number
US04900851

Reaction notes

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