Sodium Hydroxide → 2,2-Dinitropropyl methyl ether

HRID 623268Notes

Reaction equation

HRID 623268 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH:6]([N+:8]([O-:10])=[O:9])[CH3:7].[N:11]([O-:13])=[O:12].[Na+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].C(Cl)Cl>[CH3:3][O:4][CH2:5][C:6]([N+:11]([O-:13])=[O:12])([N+:8]([O-:10])=[O:9])[CH3:7]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 62655Sodium PersulfateHCID 136092852-Nitropropyl methyl etherHCID 23668193Sodium Nitrite

Product 1

HCID 143235302,2-Dinitropropyl methyl etherYield 88.1%

Reagents, catalysts & solvents 3

HCID 178511488HCID 178511488, compoundCatalystHCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g (25 mmoles) of sodium hydroxide in 10 mL of water was treated with 2.0 g (16.8 mmoles) of 2-nitropropyl methyl ether. After 10 minutes, 10 mL of methylene chloride was added, followed by a solution of 5.0 g (72 mmoles) of sodium nitrite in 10 mL of water. Next, a solution of 1.0 g (3 mmoles) of potassium ferricyanide in 5 mL of water was added, followed by 4.4 g (18 mmoles) of solid sodium persulfate. A cold water bath was used to moderate exothermic reaction. After 30 minutes, the reaction mixture was extracted with two 15 mL portions of methylene chloride. The combined extracts were washed with brine and dried over anhydrous magnesium sulfate. The solution was distilled in a short-path distillation apparatus to give 2.43 g (88% yield) of 2,2-dinitropropyl methyl ether, a colorless liquid, b.p. 100° (16 mm). 'H NMR (CDCl3): &2.18 (s. 3H, --CH3), 3.35 (s, 3H, --OCH3), 4.15 (s, 2H, --CH2O).

Workup

  1. customA cold water bath was used
  2. customreaction
  3. waitAfter 30 minutes
  4. extractionthe reaction mixture was extracted with two 15 mL portions of methylene chloride
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solution was distilled in a short-path distillation apparatus

Sources & evidence

ORD record
ord-dd4691fda5194aa9b2088f2a6621446b
Source dataset
uspto-grants-1988_09
Patent number
US04774366

Reaction notes

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