Nitric Acid → Ethyl 4-methoxy-3-nitrophenyl carbonate
Reaction equation
[C:1](=[O:14])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[O:2][CH2:3][CH3:4].C(OC(=O)C)(=O)C.[N+:22]([O-])([OH:24])=[O:23]>>[C:1](=[O:14])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([N+:22]([O-:24])=[O:23])[CH:7]=1)[O:2][CH2:3][CH3:4]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 4-methoxyphenyl carbonate (0.700 g, 3.57 mmol) was dissolved in acetic anhydride (2 mL, 21.20 mmol), and the solution was cooled to 0° C. with an ice-water bath. 65% nitric acid (0.4 mL, 5.78 mmol) was added drop-wise at the same temperature. When the addition was completed, the cold bath was removed and the resulting mixture was allowed to warm to RT and stirred for 2 hours. The reaction mixture was poured into ice-water, and the resulting precipitate was collected by filtration affording ethyl 4-methoxy-3-nitrophenyl carbonate (0.720 g, 2.99 mmol, 88% yield, MS/ESI+ 242.2 [MH]+).
Workup
- additionWhen the addition
- customthe cold bath was removed
- temperatureto warm to RT
- additionThe reaction mixture was poured into ice-water
- filtrationthe resulting precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-38903531a717436da0ce146f0e3a74aa
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09265768B2
Reaction notes
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