Methanol → Methyl 4-chloro-2-methoxybenzoate

HRID 868756Notes

Reaction equation

HRID 868756 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-1e884a77cb1745ee9cafc32c4fe2034e
Source dataset
uspto-grants-2015_03
Patent number
US08968708B2

Reaction notes

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