Acetic Acid → 4-Methoxy-2-nitrobenzoic acid

HRID 354832

Reaction equation

HRID 354832 reaction equation
C(C1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12])#N.[C:14]([OH:17])(=[O:16])[CH3:15].S(=O)(=O)(O)O>O>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:15]([C:14]([OH:17])=[O:16])=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 2886654-Methoxy-2-nitrobenzonitrile

Product 1

HCID 2886574-Methoxy-2-nitrobenzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Cyano-3-nitroanisole (52.3 g., 0.294 mole) was slowly added to a cooled solution of 53 ml. each of acetic acid, water and sulfuric acid. The solution was refluxed for 5 hours, and then diluted with 160 ml. water. After cooling, the resulting solid was filtered and dissolved in 10% sodium hydroxide solution. After decolorization with charcoal the solution was acidified with 6 N HCl, cooled and the yellow product (51.0 g., 88% yield) was filtered. An analytical sample was recrystallized from methanol/water, M.P. 196°-7° C.

Workup

  1. temperatureThe solution was refluxed for 5 hours
  2. additiondiluted with 160 ml
  3. temperatureAfter cooling
  4. filtrationthe resulting solid was filtered
  5. dissolutiondissolved in 10% sodium hydroxide solution
  6. temperaturecooled
  7. filtrationthe yellow product (51.0 g., 88% yield) was filtered
  8. customAn analytical sample was recrystallized from methanol/water, M.P. 196°-7° C.

Sources & evidence

ORD record
ord-3ed23e057fb343f18e1877779650a3a6
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Linked notes

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