Isovanillic Acid → Methyl 3-hydroxy-4-methoxybenzoate

HRID 475546Notes

Reaction equation

HRID 475546 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[C:4]([OH:5])[CH:3]=1.O.[C:14]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:5][C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:6]=1[O:7][CH3:8])[C:1]([O:12][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 12575Isovanillic AcidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 25 g quantity of isovanillic acid was suspended in 250 ml of methanol, and 1.5 g of p-toluenesulfonic acid monohydrate was added. The mixture was heated and refluxed overnight. After completion of the reaction, methanol was distilled off under reduced pressure. The residue was neutralized with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. After washing with saturated brine twice, the organic layer was separated and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 24.5 g of white crystalline methyl 3-hydroxy-4-methoxybenzoate.

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed overnight
  3. distillationwas distilled off under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washAfter washing with saturated brine twice
  6. customthe organic layer was separated
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-44c0869990194a12b13faa52117d3985
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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