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

HRID 612118Notes

Reaction equation

HRID 612118 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 5.00 g (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-c3e3f78ff42247b286dca6c846fe470a
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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