反应详情

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).

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