Nitric Acid → HCID 22933069, compound

HRID 460365Notes

Reaction equation

HRID 460365 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:16][CH2:17][CH3:18])[C:12]=1[O:13][CH2:14][CH3:15])C(O)=O)[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N+:19]([O-:21])=[O:20])[CH:10]=[C:11]([O:16][CH2:17][CH3:18])[C:12]=1[O:13][CH2:14][CH3:15])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 814323,4,5-Triethoxybenzoic acid

Product 1

HCID 22933069HCID 22933069, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,4,5-triethoxybenzoic acid (20.0 g, 78.7 mmol) in acetic acid (68 mL) was stirred at 15° C., and concentrated nitric acid (d 1.38)(34 mL, 750 mmol) was added. After stirring at room temperature for 1 hour, the reaction mixture was poured into ice water and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 3,4,5-triethoxy-1-nitrobenzene as a colorless oil (12.9 g, yield: 64%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-22fe33832f904489bcd8a348ea033422
Source dataset
uspto-grants-2007_03
Patent number
US07196101B2

Reaction notes

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