Methanol → Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

HRID 1917649Notes

Reaction equation

HRID 1917649 reaction equation
[OH:1][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:16]O>S(=O)(=O)(O)O>[OH:1][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:16])=[O:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 139156695-Hydroxy-4-methoxy-2-nitrobenzoic acid

Product 1

HCID 53396387Methyl 5-hydroxy-4-methoxy-2-nitrobenzoateYield 45%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
80 °C

Procedure

To a suspension of 5-hydroxy-4-methoxy-2-nitrobenzoic acid (8.0 g, 37.5 mmol) in methanol was added concentrated sulfuric acid (3 drops) and it was heated at 80° C. overnight. After solvent was removed under reduced pressure, to it was added water and EtOAc. The organic layer was washed with saturated NaHCO3 solution, dried over MgSO4, and concentrated under reduced pressure to afford methyl 5-hydroxy-4-methoxy-2-nitrobenzoate as a solid (3.86 g, 45%). 1H NMR (300 MHz, DMSO-d6) δ 10.96 (s, 1H), 7.63 (s, 1H), 7.08 (s, 1H), 3.91 (s, 3H), 3.81 (s, 3H).

Workup

  1. customAfter solvent was removed under reduced pressure, to it
  2. additionwas added water and EtOAc
  3. washThe organic layer was washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f14d67c6b654c1399187672e6613102
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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