Methanol → Methyl 2,3,4-trimethoxybenzoate

HRID 1703178Notes

Reaction equation

HRID 1703178 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].[CH3:16]O>S(=O)(=O)(O)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][CH3:16])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 113082,3,4-Trimethoxybenzoic acid

Product 1

HCID 13940801Methyl 2,3,4-trimethoxybenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2,3,4-trimethoxybenzoic acid (25 g) in dry methanol (250 ml), concentrated sulfuric acid (2.4 ml) was added. The reaction solution was refluxed for 20 hr, concentrated to half its volume by evaporation, and poured into a mixture of ice and water. The solution was extracted with methylene chloride and the organic extract was washed with cold aqueous sodium carbonate solution and water, dried over sodium sulfate and evaporated to give 25.4 g of 2,3,4-trimethoxybenzoic acid, methyl ester: ir (CHCl3) 1720 cm-1 ; and nmr (CDCl3) δ 3.85 (s, 3H), 3.87 (s, 3H), 3.92 (s, 6H), 6.65 (d, 1H) and 7.55 (d, 1H).

Workup

  1. temperatureThe reaction solution was refluxed for 20 hr
  2. concentrationconcentrated to half its volume by evaporation
  3. additionpoured into a mixture of ice and water
  4. extractionThe solution was extracted with methylene chloride
  5. extractionthe organic extract
  6. washwas washed with cold aqueous sodium carbonate solution and water
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-0ebed58528a34c45b381d04c9ecf842f
Source dataset
uspto-grants-1982_09
Patent number
US04351832

Reaction notes

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