Acetic Acid → 4-Methoxy-2-nitrobenzoic acid

HRID 1449559Notes

Reaction equation

HRID 1449559 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8]C=1C#N)([O-:3])=[O:2].[C:14]([OH:17])(=[O:16])[CH3:15].S(=O)(=O)(O)O>O>[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:15]=1[C:14]([OH:17])=[O:16])([O-:3])=[O:2]

Participants

5

Reactant 3

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

Product 1

HCID 2886574-Methoxy-2-nitrobenzoic acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-nitro-4-methoxybenzonitrile (14.0 g, 78.6 mM) in a solution of acetic acid (28 mL), sulfuric acid (28 mL) and water (28 mL) was refluxed for 11 hr, allowed to cool and diluted with water (200 mL). The resulting precipitate which formed was collected, washed with water and dried to give the title benzoic acid (14.2 g, 91.8%) as a yellow crystalline solid; MS(CI): 198 (M+H).

Workup

  1. temperaturewas refluxed for 11 hr
  2. temperatureto cool
  3. customThe resulting precipitate which formed
  4. customwas collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5fdd1afbc2a849fbb5871c49a8a95866
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Reaction notes

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