Methanol → Methyl 4-methyl-3-nitrobenzoate

HRID 2199962Notes

Reaction equation

HRID 2199962 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 73194-Methyl-3-nitrobenzoic acid

Product 1

HCID 81816Methyl 4-methyl-3-nitrobenzoate

Procedure

To a solution of 4-Methyl-3-nitrobenzoic acid (25.4 g) in methanol (300 mL) was slowly added concentrated sulfuric acid (2 mL), and then the reaction mixture was heated at reflux for 16 hours. The reaction mixture was concentrated under reduced pressure, and then the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give the titled compound (26.9 g) as a pale yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c341002d25ff4e5b9ad76aa5af05ba5f
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

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