Methanol → Benzoic acid, 3-formyl-4-hydroxy-, methyl ester

HRID 1739488Notes

Reaction equation

HRID 1739488 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[C:6]([OH:8])=[O:7])=[O:2].OS(O)(=O)=O.[CH3:18]O>>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[C:6]([O:8][CH3:18])=[O:7])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2717613-Formyl-4-hydroxybenzoic acid

Product 1

HCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl esterYield 84%

Procedure

A suspension of 3-formyl-4-hydroxybenzoic acid (3.9 g, 23.5 mmol) in of methanol (50 ml) was cooled below 0° C. To the suspension was added concentrated H2SO4 (3 ml) and the reaction was allowed to warm to ambient temperature and stirred for 60 hours. The reaction was heated to reflux for 12 hours, the solvent evaporated and residue subjected to chromatography (eluant: ethyl ether/hexane) to give methyl 3-formyl-4-hydroxybenzoate as a white solid (3.55 g, 84%).

Workup

  1. temperaturewas cooled below 0° C
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 12 hours
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-79253a5d10b4474191241b339924984a
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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