Acetic Acid → 4-Isopropoxy-2-methoxy-5-nitrobenzoic acid

HRID 2293540Notes

Reaction equation

HRID 2293540 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([O:14][CH3:15])[CH:6]=1)([CH3:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17].C(O)(=O)C>C(OC(=O)C)(=O)C>[CH:1]([O:4][C:5]1[C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([O:14][CH3:15])[CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 64834044-Isopropoxy-2-methoxybenzoic acid

Product 1

HCID 214770524-Isopropoxy-2-methoxy-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A 1.61 g portion of 4-isopropoxy-2-methoxybenzoic acid was dissolved in 20 ml of acetic anhydride, 0.38 ml of concentrated nitric acid and a small amount of acetic acid were added, followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured on crushed ice, extracted with chloroform and then dried over anhydrous sodium sulfate. After evaporation of the solvent under a reduced pressure, the resulting residue was dissolved in 5 ml of tetrahydrofuran and 5 ml of 1N sodium hydroxide aqueous solution, followed by stirring for 1 hour. The reaction solution was poured into 1N hydrochloric acid aqueous solution, extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1-10:1) to give 0.43 g of 4-isopropoxy-2-methoxy-5-nitrobenzoic acid.

Workup

  1. customAfter completion of the reaction
  2. additionthe reaction solution was poured
  3. customon crushed ice
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent under a reduced pressure
  7. dissolutionthe resulting residue was dissolved in 5 ml of tetrahydrofuran
  8. stirringby stirring for 1 hour
  9. additionThe reaction solution was poured into 1N hydrochloric acid aqueous solution
  10. extractionextracted with chloroform
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under a reduced pressure
  13. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1-10:1)

Sources & evidence

ORD record
ord-c99b2f4dec894224a0cdfd8b452f2a5b
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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