Nitric Acid → Methyl 5-ethoxy-4-methoxy-2-nitrobenzoate
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([O:9][CH3:10])=[O:8])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>C(O)(=O)C>[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([N+:16]([O-:18])=[O:17])=[C:6]([CH:5]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 15.0 g (74.1 mmol) of methyl 3-ethoxy-4-methoxybenzoate in 45 mL of acetic acid was treated with 15 mL of conc nitric acid dropwise over 12 min. The reaction was kept at 55° C. for 45 min, cooled to 25° C. and poured into ice water. The product was extracted into methylene chloride and the extracts were washed with water and dil sodium hydroxide, dried and evaporated. The yield was 17.8 g of methyl 5-ethoxy-4-methoxy-2-nitrobenzoate as yellow crystals: mass spectrum (electrospray, m/e): M+H 256.0.
Workup
- extractionThe product was extracted into methylene chloride
- washthe extracts were washed with water and dil sodium hydroxide
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-210e79cfa6164022b684983a2dd15c46
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288082B1
Reaction notes
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