Nitric Acid → Benzoic acid, 3,4,5-trimethoxy-2-nitro-, methyl ester

HRID 720343Notes

Reaction equation

HRID 720343 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7].[N+:17]([O-])([OH:19])=[O:18]>C(OC(=O)C)(=O)C>[N+:17]([C:10]1[C:11]([O:15][CH3:16])=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 15956Methyl 3,4,5-trimethoxybenzoate

Product 1

HCID 78765Benzoic acid, 3,4,5-trimethoxy-2-nitro-, methyl ester

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Methyl 3,4,5-trimethoxybenzoate (13.0 g) was dissolved in acetic anhydride (60 mL), a 1:20 mixed liquid (9 mL) of fuming nitric acid and concentrated nitric acid was slowly added dropwise at −10° C. to the solution, and the resultant mixture was stirred for 3 hours under ice cooling. Acetic anhydride was distilled off, water and an aqueous solution of potassium carbonate were added to the residue, and the mixture was stirred at room temperature for 40 minutes and then extracted with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain the title compound.

Workup

  1. distillationAcetic anhydride was distilled off
  2. additionwater and an aqueous solution of potassium carbonate were added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe resultant organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-eeb5160493264905987b9ca04673d514
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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