Methyl 5-methoxy-2-nitrobenzoate → 5-Methoxy-2-nitrobenzoic acid

HRID 1672323Notes

Reaction equation

HRID 1672323 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13]>C(O)C.[OH-].[Na+]>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[C:4]([CH:9]=1)[C:3]([OH:15])=[O:2]

Participants

4

Reactant 1

HCID 12719167Methyl 5-methoxy-2-nitrobenzoate

Product 1

HCID 3392095-Methoxy-2-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The crude material from Example 44b (23.3 g) is dissolved in 110 ml ethanol and 44 ml of 4N NaOH. The mixture is stirred at rt for 18 h. After that time, the ethanol is evaporated. To the residue, water is added and the mixture is washed twice with dichloromethane. To the water phase, conc. HCl is added until pH=1 is reached. The title compound is obtained by extraction with ether. Purification follows by crystallization from ethyl acetate-hexane. mp: 131-134° C.; MS: 196 (M+−1); HPLC: tret=7.90 min (Grad 1).

Workup

  1. customAfter that time, the ethanol is evaporated
  2. additionTo the residue, water is added
  3. washthe mixture is washed twice with dichloromethane
  4. additionTo the water phase, conc. HCl is added until pH=1

Sources & evidence

ORD record
ord-d4fc026c49264179b6c8cb3a7f6c1101
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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