반응 #1328407

반응 방정식

EtOAc

3,4-methylenedioxy-acetophenone

HNO3

→

4,5-methylenedioxy-2-nitroacetophenone

용매

hexane

acetic acid

반응 조건

후처리

1. 1
   기타the reaction
2. 2
   온도without external cooling from an ice bath
3. 3
   기타At temperatures below 0° C., however, the reaction
4. 4
   기타A temperature of 3–5° C.
5. 5
   workup.WAITThe mixture was left
6. 6
   workup.STIRRINGstirring for another 60 minutes at 3–5° C.
7. 7
   기타to approach ambient temperature
8. 8
   기타within 1–2 hr
9. 9
   여과the resulting yellow solid was filtered off
10. 10
    세척washed with water
11. 11
    기타suction-dried
12. 12
    기타Yield 53 g (84%), used without further purification

실험 절차

A solution of 50 g (0.305 mole) 3,4-methylenedioxy-acetophenone (Aldrich) in 200 mL glacial acetic acid was added dropwise over 30 minutes to 700 mL of cold (2–4° C.) 70% HNO3 with stirring (NOTE: the reaction will overheat without external cooling from an ice bath, which can be dangerous and lead to side products). At temperatures below 0° C., however, the reaction can be sluggish. A temperature of 3–5° C. seems to be optimal). The mixture was left stirring for another 60 minutes at 3–5° C., and then allowed to approach ambient temperature. Analysis by TLC (25% EtOAc in hexane) indicated complete conversion of the starting material within 1–2 hr. When the reaction was complete, the mixture was poured into ˜3 liters of crushed ice, and the resulting yellow solid was filtered off, washed with water and then suction-dried. Yield 53 g (84%), used without further purification.

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