Hydrogen Peroxide → HCID 20326677, compound

HRID 372770Notes

Reaction equation

HRID 372770 reaction equation
OO.FC(F)(F)[C:5]([O:7][C:8](=O)[C:9](F)(F)F)=O.[N+:16]([C:19]([N+:25]([O-:27])=[O:26])([C:23]#[N:24])[CH2:20][CH:21]=[CH2:22])([O-:18])=[O:17].P([O-])([O-])(O)=O.[Na+].[Na+]>O.C(Cl)Cl>[N+:16]([C:19]([N+:25]([O-:27])=[O:26])([C:23]#[N:24])[CH2:20][CH:21]=[CH2:22])([O-:18])=[O:17].[N+:16]([C:19]([N+:25]([O-:27])=[O:26])([C:23]#[N:24])[CH2:9][CH:8]1[O:7][CH2:5]1)([O-:18])=[O:17]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 24203Sodium Phosphate, DibasicHCID 20326684HCID 20326684, compound

Product 2

HCID 20326677HCID 20326677, compoundYield 63%HCID 20326684HCID 20326684, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of peroxytrifluoracetic acid was prepared from 1.70 ml, 0.062 moles, of 90% hydrogen peroxide, 10.5 ml, 0.074 moles, of trifluoroacetic anhydride, and 12 ml of methylene chloride. This reagent was added over a 35 minute period to a well stirred, boiling mixture of 8.2 g, 0.048 moles, of 1,1-dinitro-1-cyano-3-butene, 50 ml of methylene chloride, and 27.5 g, 0.192 moles, of disodium hydrogen phosphate. After this mild exothermic reaction had subsided, the solution was heated under reflux for 21/2 hours. The resulting mixture was stirred with 75 ml of water until all the inorganic salts had dissolved. The organic layer was separated and the aqueous layer was extracted with 2-10 ml portions of methylene chloride. The combined methylene chloride extracts were washed with 15 ml of 10% sodium bicarbonate solution and dried over magnesium sulfate. The solvent was removed at reduced pressure and the residual liquid was fractionated through a small Vigreux column to yield 3.6 g of unreacted 1,1-dinitro-1-cyano-3-butene and 3.17 g (63% yield) of 1,1-dinitro-1-cyano-3,4-epoxybutane, b.p. 62°-64°/0.005 mm., N25D 1.4672. The infrared spectrum was consistent with the assigned structure.

Workup

  1. additionThis reagent was added over a 35 minute period to
  2. additionmixture of 8.2 g, 0.048 moles
  3. customAfter this mild exothermic reaction
  4. temperaturethe solution was heated
  5. temperatureunder reflux for 21/2 hours
  6. dissolutionhad dissolved
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with 2-10 ml portions of methylene chloride
  9. washThe combined methylene chloride extracts were washed with 15 ml of 10% sodium bicarbonate solution
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-27e9e06a13324dceb288672f47150f35
Source dataset
uspto-grants-1978_05
Patent number
US04092336

Reaction notes

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