Methanol → Methyl 2-methyl-4-nitrobenzoate

HRID 2362255Notes

Reaction equation

HRID 2362255 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].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][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 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 747904-Nitro-o-toluic acid

Product 1

HCID 15088700Methyl 2-methyl-4-nitrobenzoateYield 95.3%

Conditions

Temperature
70 °C

Procedure

To a solution of 2-methyl-4-nitro-benzoic acid (3 g, 16.56 mmole) in 30 ml methanol was added at 0° C. sulfuric acid (95-98%, 10 ml) slowly for ½ hr. The reaction mixture was stirred at 70° C. for 24 hrs. Mixture was cooled down, a solid precipitated out, then the mixture was concentrated, diluted with 50 ml water, stirred for 10 minutes, filtered off, the solid was washed with water, dried to afford 3.08 g of brown solid, 95.3% yield, pure by H NMR.

Workup

  1. temperatureMixture was cooled down
  2. customa solid precipitated out
  3. concentrationthe mixture was concentrated
  4. additiondiluted with 50 ml water
  5. stirringstirred for 10 minutes
  6. filtrationfiltered off
  7. washthe solid was washed with water
  8. customdried

Sources & evidence

ORD record
ord-abdc449a88b24065a289c9d52bbcfdb7
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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