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

HRID 1917631Notes

Reaction equation

HRID 1917631 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].C(OC(=O)C)(=O)C.[N+:23]([O-])([OH:25])=[O:24]>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+:23]([O-:25])=[O:24])[CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 592192Methyl 4-ethoxy-3-methoxybenzoate

Product 1

HCID 10491210Methyl 4-ethoxy-5-methoxy-2-nitrobenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 4-ethoxy-3-methoxybenzoate (7.12 g, 33.9 mmol) and acetic anhydride (40 mL) in acetic acid (40 mL) at room temperature was dropped fume nitric acid (90%, 3.15 g). After stirring at room temperature for 15 minutes, it was heated at 50° C. for 1 hour. The reaction mixture was poured into ice and a solid was formed. It was filtered, washed with water, and dried under vacuum with P2O5 to give methyl 4-ethoxy-5-methoxy-2-nitrobenzoate as white solid (8.392 g, 97%). 1H NMR (300 MHz, CDCl3) δ 7.44 (s, 1H), 7.07 (s, 1H), 4.19 (q, 2H), 3.98 (s, 3H), 3.91 (s, 3H), 1.52 (t, 3H); LC-MS (ESI) m/z 256 (M+H)+.

Workup

  1. temperatureit was heated at 50° C. for 1 hour
  2. additionThe reaction mixture was poured into ice
  3. customa solid was formed
  4. filtrationIt was filtered
  5. washwashed with water
  6. dry with materialdried under vacuum with P2O5

Sources & evidence

ORD record
ord-5eb8d2c325d5446c81beae2fd71477ae
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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