Methanol → HCID 67467853, compound

HRID 1019749Notes

Reaction equation

HRID 1019749 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH3:16]O>OS(O)(=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 16755859(3-Methoxy-4-nitrophenyl)acetic acid

Product 1

HCID 67467853HCID 67467853, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 2-(3-methoxy-4-nitrophenyl)acetic acid (4.6 g, 21.78 mmol) and concentrated H2SO4 (2 drops) in methanol (200 mL) was heated to reflux for 3 hours. The mixture was allowed to cool to room temperature then the solvents were removed under reduced pressure. The residue was partitioned between water (100 mL) and EtOAc (100 mL), then the separated organic layer was washed with sodium bicarbonate solution (100 mL), brine (200 mL), dried (Na2SO4) and evaporated under reduced pressure to give the title compound (4.5 g, 92%) as a solid.

Workup

  1. temperatureto reflux for 3 hours
  2. customthe solvents were removed under reduced pressure
  3. customThe residue was partitioned between water (100 mL) and EtOAc (100 mL)
  4. washthe separated organic layer was washed with sodium bicarbonate solution (100 mL), brine (200 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b89fb5257c694111a67f4d04bceac5a5
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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