Methanol → Methyl 2-methyl-3-nitrobenzoate

HRID 2182729Notes

Reaction equation

HRID 2182729 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-bc03114a32ff48178f363b2bdeeb8568
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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