Gallic Acid → Methyl Gallate

HRID 531420Notes

Reaction equation

HRID 531420 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.S(=O)(=O)(O)O.[CH:18](OC)(OC)OC>CO>[C:1]([O:12][CH3:18])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1

Participants

5

Reactant 3

HCID 370Gallic AcidHCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformate

Product 1

HCID 7428Methyl GallateYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution in which gallic acid (5.0 g, 29.39 mmol) was dissolved in methanol (25 mL), concentrated sulfuric acid (0.5 mL) and trimethyl orthoformate (3.21 mL, 88.17 mmol) were added consecutively at room temperature. The reaction mixture was heated under reflux for 10 hours, cooled to room temperature, and methanol was removed by vacuum distillation. To the residue obtained as above, distilled water (10 mL) was added, and the precipitated solid was filtered to give methyl gallate (5.15 g, 95%). 1H NMR (500 MHz, DMSO-D6) δ 9.29 (s, 2H), 8.96 (s, 1H), 6.92 (s, 2H), 3.73 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 10 hours
  3. custommethanol was removed by vacuum distillation
  4. customTo the residue obtained as above,
  5. distillationdistilled water (10 mL)
  6. additionwas added
  7. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-044e233c4efc4d03ba667d8ac3009393
Source dataset
uspto-grants-2016_05
Patent number
US09354234B2

Reaction notes

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