Methanol → Methyl 2-methyl-4-nitrobenzoate

HRID 2280333Notes

Reaction equation

HRID 2280333 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-267ccf42b7974e09a048ae29980b9e3b
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

Loading…