Methanol → 2-(4-Methoxy-phenoxy)-5-nitro-benzoic acid methyl ester

HRID 47437Notes

Reaction equation

HRID 47437 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH3:22]O>S(=O)(=O)(O)O>[CH3:22][O:11][C:10](=[O:12])[C:9]1[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:8]=1[O:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 28008662-(4-methoxyphenoxy)-5-nitrobenzoic acid

Product 1

HCID 540755342-(4-Methoxy-phenoxy)-5-nitro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

2-(4-Methoxy-phenoxy)-5-nitro-benzoic acid (2.5 g), (DE 2058295) in methanol (75 ml) containing conc. sulfuric acid (3 drops) was boiled for 16 h. Solvent was removed at reduced pressure, the residue dissolved in ethyl acetate and washed with aqueous sodium hydrogen carbonate. The organic phase was dried (Na2SO4) and solvent removed at reduced pressure to give 2-(4-methoxy-phenoxy)-5-nitro-benzoic acid methyl ester (2.50 g). m/z (API+): 304 (MH+).

Workup

  1. customSolvent was removed at reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with aqueous sodium hydrogen carbonate
  4. dry with materialThe organic phase was dried (Na2SO4) and solvent
  5. customremoved at reduced pressure

Sources & evidence

ORD record
ord-fcd65e698cba4ce88f7661c0861eb09c
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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