Methanol → Methyl 2-methyl-4-nitrobenzoate

HRID 1947627Notes

Reaction equation

HRID 1947627 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14]O>S(=O)(=O)(O)O>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 747904-Nitro-o-toluic acid

Product 1

HCID 15088700Methyl 2-methyl-4-nitrobenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-Methyl-4-nitrobenzoic acid (2.00 g, 11.00 mmol) was stirred in concentrated sulfuric acid (0.6 ml) and methanol (25 ml) at reflux for 15 hrs. Reaction was cooled and the solvent evaporated. The resulting residue was partitioned between water and dichloromethane and the organic phase separated. The aqueous phase was extracted with dichloromethane (×3) and the combined organics washed with brine, then dried (MgSO4) and evaporated in vacuo to yield the title compound as a pale yellow solid (1.89 g, 96%). HPLC retention time 4.39 min.

Workup

  1. customReaction
  2. temperaturewas cooled
  3. customthe solvent evaporated
  4. customThe resulting residue was partitioned between water and dichloromethane
  5. customthe organic phase separated
  6. extractionThe aqueous phase was extracted with dichloromethane (×3)
  7. washthe combined organics washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-c06cff6edf4f4c42af6c4b51b912e4db
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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