Sodium Hydroxide → 6-Hydroxy-4,4-dimethylhexane-1,2-diyl dinitrate

HRID 1676005Notes

Reaction equation

HRID 1676005 reaction equation
[N+](C1C=CC(C([O:10][CH2:11][CH2:12][C:13]([CH3:26])([CH3:25])[CH2:14][CH:15]([O:21][N+:22]([O-:24])=[O:23])[CH2:16][O:17][N+:18]([O-:20])=[O:19])=O)=CC=1)([O-])=O.[OH-].[Na+]>C1COCC1.CCO.C(=O)(O)[O-].[Na+]>[N+:18]([O-:20])([O:17][CH2:16][CH:15]([O:21][N+:22]([O-:24])=[O:23])[CH2:14][C:13]([CH3:26])([CH3:25])[CH2:12][CH2:11][OH:10])=[O:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 582094543,3-Dimethyl-5,6-bis(nitrooxy)hexyl 4-nitrobenzoate

Product 1

HCID 597787456-Hydroxy-4,4-dimethylhexane-1,2-diyl dinitrate

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 3,3-dimethyl-5,6-bis(nitrooxy)hexyl 4-nitrobenzoate (1.9 g, 4.73 mmol) in THF:EtOH 1:1 (12 ml) a aqueous solution of NaOH 3N (3.8 ml, 11.4 mmol) was added and the mixture was stirred at room temperature for 3 hrs. Then the mixture was diluted with a saturated solution of sodium bicarbonate and the product was extracted with EtOAc (3×30 ml). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure, affording the title compound which was used in the subsequent step without further purification.

Workup

  1. extractionthe product was extracted with EtOAc (3×30 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a7fb8c7b8e348bba5198b718f1aa3a2
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

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