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

HRID 871232Notes

Reaction equation

HRID 871232 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-1e8fe4f1966643a08483bf776172cab6
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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