Hydrochloric Acid → Methyl 3-chloro-4-hydroxy-5-methoxybenzoate

HRID 1665194Notes

Reaction equation

HRID 1665194 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[C:4]([O:11][CH3:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl.[CH3:15]O>>[CH3:15][O:8][C:7](=[O:9])[C:6]1[CH:5]=[C:4]([O:11][CH3:12])[C:3]([OH:13])=[C:2]([Cl:1])[CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 442153-Chloro-4-hydroxy-5-methoxybenzoic acid

Product 1

HCID 71004Methyl 3-chloro-4-hydroxy-5-methoxybenzoate

Procedure

A mixture of 5-chlorovanillic acid (5.0 g, 24.6 mmol) and conc. HCl (5 ml) in MeOH (100 ml) is heated at reflux for 48 hours. The solvent is removed in vacuo and water is added to the residue to yield a white precipitate, which is collected by filtration, washed with water, and then dissolved in Et2O. The solution is dried (Na2SO4) and the solvent removed in vacuo to yield 3-Chloro-4-hydroxy-5-methoxy-benzoic acid methyl ester as a white solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 48 hours
  3. customThe solvent is removed in vacuo and water
  4. additionis added to the residue
  5. customto yield a white precipitate, which
  6. filtrationis collected by filtration
  7. washwashed with water
  8. dissolutiondissolved in Et2O
  9. dry with materialThe solution is dried (Na2SO4)
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cde50feae51e4cb8898fe94432a639bb
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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