4,4,4-Trinitro-1-butanol → 4,4-Dinitrobutan-1-ol

HRID 1199507Notes

Reaction equation

HRID 1199507 reaction equation
[N+:1]([C:4]([N+]([O-])=O)([N+:9]([O-:11])=[O:10])[CH2:5][CH2:6][CH2:7][OH:8])([O-:3])=[O:2]>CO>[N+:1]([CH:4]([N+:9]([O-:11])=[O:10])[CH2:5][CH2:6][CH2:7][OH:8])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 138979744,4,4-Trinitro-1-butanol

Product 1

HCID 144017664,4-Dinitrobutan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This alcohol was prepared by stirring 4,4,4-trinitro-1-butanol (554 g, 2.65 mol) in methanol (6 l) with KI (1426 g, 8.6 mol) for 6 days at room temperature. The precipitated potassium salt was filtered, suspended in water (4 L), acidified with concentrated HCl (250 ml), and extracted into CH2Cl2 (6×500 ml). The extracts were washed with 10% NaHSO3 (1000 ml). The solution was dried over anhydrous MgSO4 and concentrated to give the product (220 g, 51%) as a yellow oil. The infrared spectrum had peaks at 3450, 2950, 1575, 1340, and 1070 cm-1.

Workup

  1. filtrationThe precipitated potassium salt was filtered
  2. extractionextracted into CH2Cl2 (6×500 ml)
  3. washThe extracts were washed with 10% NaHSO3 (1000 ml)
  4. dry with materialThe solution was dried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b0e4a0b7e33c4beab2bd19dc805f078b
Source dataset
uspto-grants-1990_02
Patent number
US04900851

Reaction notes

Loading…