Methanol → Methyl 2-methyl-3-nitrobenzoate

HRID 2055010Notes

Reaction equation

HRID 2055010 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].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[CH3:1]

Participants

4

Reactant 3

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

Product 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate

Procedure

20 g (110.4 mmol) of 2-methyl-3-nitrobenzoic acid is refluxed in 100 ml of methanol for 10 hours after 2 ml of concentrated sulfuric acid is added. The product that crystallizes out during cooling is suctioned off and dried. The filtrate is evaporated to the dry state, the solid residue is taken up in ethyl acetate, and the solution is washed twice with saturated sodium bicarbonate solution. After drying on Na2SO4, another product is obtained. Together, 16.4 (76.3%) of the desired compound is obtained.

Workup

  1. additionis added
  2. customThe product that crystallizes out
  3. temperatureduring cooling
  4. customdried
  5. customThe filtrate is evaporated to the dry state
  6. washthe solution is washed twice with saturated sodium bicarbonate solution
  7. customAfter drying on Na2SO4
  8. customanother product is obtained

Sources & evidence

ORD record
ord-59074f6d244e4f2aab341ee4e1fa71da
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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