1,1-Dichloroethane → HCID 14816499, compound

HRID 1904155Notes

Reaction equation

HRID 1904155 reaction equation
[CH:1]([N+:8]([O-:10])=[O:9])([N+:5]([O-:7])=[O:6])[N+:2]([O-:4])=[O:3].ClC(Cl)C.C[Si](C)(C)[O:17][CH2:18][CH2:19][O:20][CH2:21]I.ICOCI>CN(C)C=O.ClCCCl.C(Cl)Cl>[OH:17][CH2:18][CH2:19][O:20][CH2:21][C:1]([N+:8]([O-:10])=[O:9])([N+:5]([O-:7])=[O:6])[N+:2]([O-:4])=[O:3]

Participants

8

Reactant 4

HCID 63651,1-DichloroethaneHCID 10602Trinitromethane2×HCID 598725Bis(iodomethyl)etherHCID 14816496HCID 14816496, compound

Product 1

HCID 14816499HCID 14816499, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

As illustrated by example 3, a dry solution of nitroform in a suitable inert organic solvent such as methylene chloride, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2-dichloroethane, etc., is added slowly to the iodomethyl 2-(trimethylsilyloxy)ethyl ether solution while the temperature of the solution is maintained in the range of from -50° C. to -80° C., and preferably from -70° C. to -80° C. Next, dry dimethylformamide is added to ionize the nitroform so that it will react with the iodomethyl ether. The solution is then allowed to warm slowly to a temperature of from about -5° C. to about +5° C. where it is kept until the reaction is completed. Pouring into ice water and then extraction into an organic solvent (e.g., methylene chloride) yields a crude 2,2,2-trinitroethyl 2-hydroxyethyl ether mixture.

Workup

  1. temperatureis maintained in the range of from -50° C. to -80° C.
  2. custompreferably from -70° C. to -80° C
  3. temperatureto warm slowly to a temperature of from about -5° C. to about +5° C. where it
  4. extractionextraction into an organic solvent (e.g., methylene chloride)

Sources & evidence

ORD record
ord-c558b83156cb41f988a703a2916fb86a
Source dataset
uspto-grants-1989_06
Patent number
USH0000644

Reaction notes

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