Acetic Acid → Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

HRID 480030Notes

Reaction equation

HRID 480030 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].OS(O)(=O)=O.[C:21](=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CO>[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][CH3:21])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 139156695-Hydroxy-4-methoxy-2-nitrobenzoic acid

Product 1

HCID 53396387Methyl 5-hydroxy-4-methoxy-2-nitrobenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-hydroxy-4-methoxy-2-nitrobenzoic acid [Sinha J. Ind. Chem. Soc., 47, 925 (1970)] (83.0 g, 0.39 mol) in MeOH (250 ml) was added concentrated H2SO4 (20 ml) and the reaction mixture was heated to reflux for 16 h. On cooling, the reaction mixture was poured into aqueous potassium carbonate solution and acetic acid was added until pH 4 was reached. The mixture was extracted with chloroform, the organic layer washed twice with H2O and dried over MgSO4. Evaporation under reduced pressure afforded the subtitle compound as yellow crystals (77.0 g, 87%). Rf 0.30 (benzene/acetone 4/1, v/v); m.p. 146-9° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. temperatureOn cooling
  4. additionwas added until pH 4
  5. extractionThe mixture was extracted with chloroform
  6. washthe organic layer washed twice with H2O
  7. dry with materialdried over MgSO4
  8. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-04447f87d8504f11bdeaad9284565d66
Source dataset
uspto-grants-2003_11
Patent number
US06649620B2

Reaction notes

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