Methanol → Methyl 4-methyl-3-nitrobenzoate

HRID 1788465Notes

Reaction equation

HRID 1788465 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14]O>>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 73194-Methyl-3-nitrobenzoic acid

Product 1

HCID 81816Methyl 4-methyl-3-nitrobenzoateYield 99%

Procedure

4-Methyl-3-nitro benzoic acid (12.5 g, 69 mmol) was dissolved in anhydrous methanol (500 mL) in a 1 L flask. HCl gas was then bubbled through the solution until saturation (3 h). The HCl source was then removed, and the reaction was stirred at room temperature overnight. The reaction was then concentrated to dryness and dried over phosphorus pentoxide overnight to yield 13.34 g (99%) of product which was 99% pure by QC HPLC.

Workup

  1. customHCl gas was then bubbled through the solution until saturation (3 h)
  2. customThe HCl source was then removed
  3. concentrationThe reaction was then concentrated to dryness
  4. dry with materialdried over phosphorus pentoxide overnight

Sources & evidence

ORD record
ord-996865c270684c3fb0cde1f265a144da
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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