Sulfuric Acid → Methyl 2-methyl-5-nitrobenzoate

HRID 1010530Notes

Reaction equation

HRID 1010530 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[C:19](=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[CH3:19][O:10][C:9](=[O:11])[C:8]1[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:7]=1[CH3:6]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 μl of concentrated sulfuric acid is added to a suspension of 2 g of 2-methyl-5-nitrobenzoic acid in 7 ml of methanol. It is refluxed for 6 hours. Then, the reaction mixture is diluted with ethyl acetate and poured into saturated sodium bicarbonate solution. The phases are separated, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are then washed with saturated sodium chloride solution, dried on sodium sulfate, and concentrated by evaporation in a vacuum. The crude product that is obtained is incorporated without purification into the next step.

Workup

  1. temperatureIt is refluxed for 6 hours
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washThe combined organic phases are then washed with saturated sodium chloride solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-9f3ef140df0544a784a50b21f1504c2d
Source dataset
uspto-grants-2011_07
Patent number
US07977325B2

Reaction notes

Loading…