Carbon Dioxide → HCID 12507563, compound

The pure allyl 2,2-dinitroethyl ether, prepared according to the procedure set forth in Example 1, was added (4.11 grams; 0.0234 mole) slowly to a well stirred solution of sodium hydroxide (0.935 grams; 0.0234 mole), water (15 mls) and methanol (34 mls). The slightly exothermic reaction yielded an immediate orange color. The final pH was approximately 8. Perchloryl fluoride was then metered into the system to which was added a dry ice reflux condenser to prevent excess perchloryl fluoride from sweeping out of the reaction flask. When the perchloryl fluoride began to reflux vigorously, it was shut off and under slight nitrogen flow reflux was maintained for about 4 hours. The reaction temperature was maintained between 20°-25° C. with a water bath. The reaction mixture changed from deep orange to pale orange in color. Water (50 mls) was added and a yellow oil dropped out of solution. The mixture was then extracted with three 60 ml portions of methylene chloride. The methylene chloride extracts were washed with three 30 ml portions of 3 percent sodium hydroxide and finally with water. After drying with magnesium sulfate, excess methylene chloride was removed under vacuum and the residual liquid was distilled through a small Vigreux column. The distillation yielded 2.4 grams (53% yield) of allyl 2,2-dinitro-2-fluoroethyl ether, b. p. 42° C./1.1 mm, nD25 1.4240, d25 1.28. The calculated elemental analysis for C5H7N2O5 was C, 30.93; H, 3.64; N, 14.43. The found analysis was C, 30.85; H, 3.45; N, 14.43. The infrared spectrum for the compound, in Nujol, exhibited maximum peaks at 6.2, 7.6 and 9.0 microns.

1. additionwas added (4.11 grams; 0.0234 mole) slowly to a well
2. customThe slightly exothermic reaction
3. customyielded an immediate orange color
4. temperaturereflux condenser
5. temperatureto reflux vigorously
6. temperaturereflux
7. temperaturewas maintained for about 4 hours
8. temperatureThe reaction temperature was maintained between 20°-25° C. with a water bath
9. additiona yellow oil dropped out of solution
10. extractionThe mixture was then extracted with three 60 ml portions of methylene chloride
11. washThe methylene chloride extracts were washed with three 30 ml portions of 3 percent sodium hydroxide and finally with water
12. dry with materialAfter drying with magnesium sulfate, excess methylene chloride
13. customwas removed under vacuum
14. distillationthe residual liquid was distilled through a small Vigreux column
15. distillationThe distillation

ORD record

ord-28076ddf162d41348faf2d80c4815eb9

Source dataset

uspto-grants-1979_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04141768