Methanol → Methyl 2-methyl-5-nitrobenzoate

HRID 1919663Notes

Reaction equation

HRID 1919663 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoateYield 74%

Procedure

2-methyl-5-nitrobenzoic acid (24 g) was dissolved in methanol (240 ml) and concentrated sulfuric acid (8 ml). The mixture was stirred at reflux overnight. Upon cooling the ester crystallized out. The material was isolated by filtration to afford methyl 2-methyl-5-nitrobenzoate as a white solid (19.0 g, 74% yield). A second crop of material (4.92 g, 19% yield) was isolated upon concentration and addition of water to the mother liquor.

Workup

  1. temperatureat reflux overnight
  2. customcrystallized out
  3. customThe material was isolated by filtration

Sources & evidence

ORD record
ord-fb30efd7e36a47a19fc9c848cc27dcc2
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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