反応 #1328407

反応方程式

EtOAc

3,4-methylenedioxy-acetophenone

HNO3

→

4,5-methylenedioxy-2-nitroacetophenone

溶媒

hexane

acetic acid

反応条件

後処理

1. 1
   その他the reaction
2. 2
   温度without external cooling from an ice bath
3. 3
   その他At temperatures below 0° C., however, the reaction
4. 4
   その他A 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
   その他to approach ambient temperature
8. 8
   その他within 1–2 hr
9. 9
   ろ過the resulting yellow solid was filtered off
10. 10
    洗浄washed with water
11. 11
    その他suction-dried
12. 12
    その他Yield 53 g (84%), used without further purification

実験手順

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.

出典