Trifluoroacetic acid → (2,2,2-Trinitroethoxy)ethene

HRID 2295906Notes

Reaction equation

HRID 2295906 reaction equation
[CH:1](OC=C)=[CH2:2].[N+:6]([C:9]([N+:15]([O-:17])=[O:16])([N+:12]([O-:14])=[O:13])[CH2:10][OH:11])([O-:8])=[O:7].FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]([O:11][CH2:10][C:9]([N+:12]([O-:14])=[O:13])([N+:15]([O-:17])=[O:16])[N+:6]([O-:8])=[O:7])=[CH2:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8024Vinyl etherHCID 61233Ethanol, 2,2,2-trinitro-

Product 1

HCID 15743368(2,2,2-Trinitroethoxy)etheneYield 25.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure described in Examples I and II, divinyl ether and 2,2,2-trinitroethanol (X) were reacted for 60.25 hours in methylene chloride in the presence of red mercuric oxide and trifluoroacetic acid. A 25.9% yield of 2,2,2-trinitroethyl vinyl ether was obtained after elution with carbon tetrachloride through the neutral alumina (pH 7.3) column, followed by column chromatographic removal of 2,2,2-trinitroethanol in hexane through 60/200 mesh SiO2.

Sources & evidence

ORD record
ord-e5b987bedf784d25a665e2141cd29780
Source dataset
uspto-grants-1984_01
Patent number
US04426540

Reaction notes

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