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

HRID 2365580Notes

Reaction equation

HRID 2365580 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-a869beb75e2d4fd1a84c53f04fd7578a
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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