Methanol → Methyl 3-hydroxy-4-methoxybenzoate

HRID 840143Notes

Reaction equation

HRID 840143 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 12575Isovanillic Acid

Product 1

HCID 4056967Methyl 3-hydroxy-4-methoxybenzoateYield 91%

Procedure

To a suspension of 3-hydroxy-4-methoxy benzoic acid (33.63 g, 0.2 mol) in MeOH (500 ml) was added concentrated sulphuric acid (25 ml) and the reaction mixture was heated to reflux for 2 h. On cooling the reaction mixture was concentrated under reduced pressure to 100 ml and the residue was extracted with EtOAc. The organic layer was washed sequentially with H2O (×2), saturated aqueous sodium bicarbonate and saturated brine, dried over MgSO4 and evaporated under reduced pressure, to afford the subtitle compound as colourless crystals (33.0 g, 91%). Rf 0.59 (EtOAc). MS m/z 183 (MH+).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. temperatureOn cooling the reaction mixture
  4. concentrationwas concentrated under reduced pressure to 100 ml
  5. extractionthe residue was extracted with EtOAc
  6. washThe organic layer was washed sequentially with H2O (×2), saturated aqueous sodium bicarbonate and saturated brine
  7. dry with materialdried over MgSO4
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fae19916fa1946b396adb3ac4c508c08
Source dataset
uspto-grants-2002_04
Patent number
US06365599B1

Reaction notes

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