Nitric Acid → Methyl 4-ethoxy-5-methoxy-2-nitrobenzoate

HRID 1595741Notes

Reaction equation

HRID 1595741 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:14][CH3:15])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>C(O)(=O)C>[CH2:1]([O:3][C:4]1[C:5]([O:14][CH3:15])=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:12]([N+:16]([O-:18])=[O:17])[CH:13]=1)[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 592192Methyl 4-ethoxy-3-methoxybenzoate

Product 1

HCID 10491210Methyl 4-ethoxy-5-methoxy-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Dissolved 5.00g (23.7 mmol) methyl 4-ethoxy-3-methoxybenzoate in 25 ml acetic acid under N2 and added 6.1 ml (95.1 mmol) 69% nitric acid dropwise over 30 minutes. Heated to 50° C. for 1.5 hours and poured onto ice bath. Extracted with chloroform, washed with dilute sodium hydroxide solution and filtered through magnesium sulfate. Stripped solvent and dried in vacuo, giving 5.268 of off-white solid: mass spectrum (electrospray m/e): M+H=255.8.

Workup

  1. additionpoured onto ice bath
  2. extractionExtracted with chloroform
  3. washwashed with dilute sodium hydroxide solution
  4. filtrationfiltered through magnesium sulfate
  5. customdried in vacuo
  6. customgiving 5.268 of off-white solid

Sources & evidence

ORD record
ord-fc4202cca3204f14a061d581b4238694
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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