Nitric Acid → 2,2,2-Trinitroethyl 2-nitroxyethyl ether

HRID 1904157Notes

Reaction equation

HRID 1904157 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[N+:7]([O-:9])=[O:8].[N+:16]([O-])([OH:18])=[O:17].S(=O)(=O)(O)O>C(Cl)Cl>[O:1]([CH2:2][CH2:3][O:4][CH2:5][C:6]([N+:13]([O-:15])=[O:14])([N+:7]([O-:9])=[O:8])[N+:10]([O-:12])=[O:11])[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14816499HCID 14816499, compound

Product 1

HCID 141217732,2,2-Trinitroethyl 2-nitroxyethyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The dried solution of 2,2,2-trinitroethyl 2-hydroxyethyl ether produced in example 3 was diluted to 200 ml with methylene chloride and this solution was slowly added with cooling below 5° C. (ice bath) to a vigorously stirred nitrating solution (prepared by slowly adding 136 ml of 90% nitric acid to 272 ml of concentrated sulfuric acid with cooling). The nitration mixture was vigorously stirred at room temperature for 3 hours before it was poured onto ice. The organic layer was separated, washed with 3×100 ml of water, dried over magnesium sulfate and allowed to stand in a hood to evaporate volatiles to give 75 g (65%) of essentially pure 2,2,2-trinitroethyl 2-nitroxyethyl ether (TNEN). The TNEN can be further purified by dissolving it in 300 ml of diethyl ether, adding 300 ml of hexanes, cooling the solution in a dry ice-acetone bath until it begins to cloud, adding seed crystals, continuing cooling in the dry ice-acetone bath for 20 minutes, removing the crystals by filtration through a precooled filter funnel, washing the crystals with cold (-40° C.) hexanes and quickly redissolving the cold crystals into methylene chloride. The pure product has mp 10°-11° C.; 1H NMR (CDCl3): δ4.10 (m,2H), 4.70 (m,2H) 4.88 (s,2H).

Workup

  1. additionthis solution was slowly added
  2. temperaturewith cooling below 5° C. (ice bath) to a vigorously stirred nitrating solution (
  3. customprepared
  4. temperaturewith cooling)
  5. additionwas poured onto ice
  6. customThe organic layer was separated
  7. washwashed with 3×100 ml of water
  8. dry with materialdried over magnesium sulfate
  9. customto evaporate volatiles

Sources & evidence

ORD record
ord-adb9167f12244329b5cf64455e64644a
Source dataset
uspto-grants-1989_06
Patent number
USH0000644

Reaction notes

Loading…