Methanol → Methyl 2,3,4-trimethoxybenzoate

HRID 2084828Notes

Reaction equation

HRID 2084828 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:21]O>>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH3:21])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 113082,3,4-Trimethoxybenzoic acid

Product 1

HCID 13940801Methyl 2,3,4-trimethoxybenzoate

Conditions

Temperature
80 °C

Procedure

2,3,4-trimethoxybenzoic acid (7.3 g) was dissolved in methanol (73 ml), mixed with sulfuric acid (15 ml), and stirred for 3 hours while heating at 80° C. The resultant was allowed to stand for cooling, evaporated under reduced pressure for removing the solvent, and the residue was added to cold water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate water and then with a saturated aqueous sodium chloride solution, dried over sodium sulfate anhydride, and evaporated under reduced pressure for removing the solvent to give Compound IIbt-a (6.8 g, 87%) as a colorless oily substance.

Workup

  1. temperaturefor cooling
  2. customevaporated under reduced pressure
  3. customfor removing the solvent
  4. additionthe residue was added to cold water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated sodium bicarbonate water
  7. dry with materialwith a saturated aqueous sodium chloride solution, dried over sodium sulfate anhydride
  8. customevaporated under reduced pressure
  9. customfor removing the solvent
  10. customto give Compound IIbt-a (6.8 g, 87%) as a colorless oily substance

Sources & evidence

ORD record
ord-5a90f14d0ad44aa99b4b7c78c8b647c2
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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