Syntheses of Some Stable Radicals and the Most Important Intermediates

  • E. G. Rozantsev
  • H. Ulrich

Abstract

A five-liter glass vessel was charged with 2500 g of dry acetone, 800 g of ground anhydrous calcium chloride, and 255 g of liquid ammonia. The reaction mixture was left to stand for four days with periodic stirring. Then, with continuous cooling and stirring, the mixture was carefully decomposed with 1250 ml of 50% caustic soda solution. The organic layer was separated and the aqueous layer was carefully extracted with diethyl ether. The diethyl ether extract was combined with the organic layer. After the combined mixture had been dried with anydrous potassium carbonate, the solvent was distilled off, the residue was subjected to vacuum rectification* through a column with an efficiency of 10 theoretical plates, and the fraction boiling between 84 and 90°C (14 mm Hg) was collected. The distillate was cooled and the deposited crystals of triacetoneamine were collected on a glass filter. The yield of pure substance was 350–380 g (15–17%) after recrystallization from cyclohexane: colorless needles, mp 35.5–36°C; bp 84–85°C (15 mm Hg), 102–105°C (18 mm Hg).

Keywords

Potassium Carbonate Stable Radical Thionyl Chloride Dilute Hydrochloric Acid Caustic Soda 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Science+Business Media New York 1970

Authors and Affiliations

  • E. G. Rozantsev
    • 1
  • H. Ulrich
    • 2
  1. 1.Institute of Chemical PhysicsAcademy of Sciences of the USSRMoscowUSSR
  2. 2.Donald S. Gilmore Research LaboratoriesThe Upjohn CompanyNorth HavenUSA

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