Dichloromethane → 1-(Ethenyloxy)-2,2-dinitropropane

HRID 2295905Notes

Reaction equation

HRID 2295905 reaction equation
C(Cl)Cl.[CH:4](OC=C)=[CH2:5].[N+:9]([C:12]([N+:16]([O-:18])=[O:17])([CH3:15])[CH2:13][OH:14])([O-:11])=[O:10].FC(F)(F)C(O)=O>C(Cl)(Cl)(Cl)Cl.O>[CH:4]([O:14][CH2:13][C:12]([N+:16]([O-:18])=[O:17])([N+:9]([O-:11])=[O:10])[CH3:15])=[CH2:5]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 8024Vinyl etherHCID 701942,2-Dinitropropanol

Product 1

HCID 123859281-(Ethenyloxy)-2,2-dinitropropaneYield 58.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A 50 ml single necked, round bottom flask was charged with 20 ml methylene chloride, 0.50 g (7.14 mmole) divinyl ether, 1.07 g (7.14 mmole) 2,2-dinitropropanol (VIII), and 0.1 g red mercuric oxide. The solution was stirred, using a Teflon coated magnetic bar while 100 μl trifluoroacetic acid was added. The reaction flask was then fitted with a water cooled reflux condenser and drying tube filled with Drierite desiccant. The reaction was stirred under reflux (~37° C.) for 16 hours. The methylene chloride solvent was removed in vacuo, leaving a slightly yellow, clear oil. The oil was taken up in 2 ml carbon tetrachloride and placed onto 7.8 g neutral alumina (pH 6.9) packed with carbon tetrachloride into a 15 ml "course" glass sintered funnel. The carbon tetrachloride was removed in vacuo, leaving 0.74 g of crude 2,2-dinitropropyl vinyl ether (IX) which was shown by nuclear resonance spectrometry to be 92 percent pure.

Workup

  1. additionwas added
  2. temperaturecooled
  3. temperaturereflux condenser
  4. customdrying tube
  5. additionfilled with Drierite desiccant
  6. stirringThe reaction was stirred
  7. temperatureunder reflux (~37° C.) for 16 hours
  8. customThe methylene chloride solvent was removed in vacuo
  9. customleaving a slightly yellow, clear oil
  10. customThe carbon tetrachloride was removed in vacuo

Sources & evidence

ORD record
ord-1d82b5865c2d44178bb960f121bc7a9a
Source dataset
uspto-grants-1984_01
Patent number
US04426540

Reaction notes

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