Methanol → Methyl 2-methyl-3-nitrobenzoate

HRID 486265Notes

Reaction equation

HRID 486265 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(Cl)(Cl)=O.[CH3:18]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][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 160962-Methyl-3-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate

Procedure

To 2-methyl-3-nitrobenzoic acid (10.0 g) is added methanol (100 ml) and thereto thionyl chloride (8 ml) is added dropwise at room temperature. After reflux for 2 hours, the reaction mixture is poured into ice-water and extracted with dichloromethane. The solvent is concentrated to give methyl 2-methyl-3-nitrobenzoate (10.8 g).

Workup

  1. temperatureAfter reflux for 2 hours
  2. extractionextracted with dichloromethane
  3. concentrationThe solvent is concentrated

Sources & evidence

ORD record
ord-d11d056919ab40c5b9b2556c4f6435a1
Source dataset
uspto-grants-1994_03
Patent number
US05290934

Reaction notes

Loading…