Methanol → Methyl 2-methyl-3-nitrobenzoate

HRID 2208938Notes

Reaction equation

HRID 2208938 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:19]O>>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 160962-Methyl-3-nitrobenzoic acid

Product 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate

Conditions

Temperature
60 °C

Procedure

To a solution of 2-methyl-3-nitrobenzoic acid (10.0 g, 55.0 mmol) in 120 ml of methanol, was added conc. H2SO4 (15 ml) at room temperature and the mixture stirred at 60° C. overnight. The mixture was concentrated under reduced pressure, the crude material was neutralized with sat. NaHCO3, and extracted with ethyl acetate. The organic phase was dried over Na2SO4, and concentrated under reduced pressure to afford the title compound (10 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79f97f1259a24304aa4b66d3cc7ece07
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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