Реакция #725654

Уравнение реакции

1-Dodecene

nitric acid

→

1-nitro-2-dodecene

Условия реакции

Обработка

1. 1
   Температураthen cooled to room temperature
2. 2
   ДругоеThe organic layer separated
3. 3
   Промывкаwashed with a saturated sodium chloride solution (3×75 mL)
4. 4
   СушкаAfter drying over magnesium sulfate
5. 5
   Фильтрацияfiltering
6. 6
   workup.DISTILLATIONdistilled (0.5 Torr, 36° C.) which
7. 7
   Другоеremoved unreacted 1-dodecene
8. 8
   workup.ADDITIONcontaining 1-nitro-2-dodecene and 1-nitro-2-dodecanol
9. 9
   ДругоеThis oil was further reacted with methanesulfonyl chloride and triethylamine

Методика

1-Dodecene (222 mL, 1.0 mole) and concentrated nitric acid (96 mL, 1.5 moles) were mixed together at room temperature. The solution was heated to 100° C. for 4 hours with rapid stirring then cooled to room temperature. The organic layer separated and washed with a saturated sodium chloride solution (3×75 mL). After drying over magnesium sulfate and filtering, the orange oil was vacuum distilled (0.5 Torr, 36° C.) which removed unreacted 1-dodecene. The remaining orange/red oil is a mixture containing 1-nitro-2-dodecene and 1-nitro-2-dodecanol. This oil was further reacted with methanesulfonyl chloride and triethylamine to dehydrate the alcohol and produce more 1-nitro-2-dodecene. After this dehydration step, the structure of 1-nitro-2-dodecene was confirmed by IR and GC analysis.

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