Methanol → Methyl 4-chloro-2-methoxybenzoate

HRID 1625581Notes

Reaction equation

HRID 1625581 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13]O>OS(O)(=O)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 936824-Chloro-o-anisic acid

Product 1

HCID 327084Methyl 4-chloro-2-methoxybenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A suspension of 4-chloro-2-methoxybenzoic acid (5 g, 27 mmol) in MeOH (18 mL) and conc. H2SO4 (1.5 mL) was refluxed overnight. MeOH was evaporated and the residue was extracted to EtOAc and successively washed with water and brine, dried over MgSO4, filtered and evaporated to give methyl 4-chloro-2-methoxybenzoate as a white solid (5.17 g, 96%).

Workup

  1. temperaturewas refluxed overnight
  2. customMeOH was evaporated
  3. extractionthe residue was extracted to EtOAc
  4. washsuccessively washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-35683c0c1bac4d0186e085f4d11a2c02
Source dataset
uspto-grants-2014_07
Patent number
US08784782B2

Reaction notes

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