Gallic Acid → Methyl Gallate

HRID 465927Notes

Reaction equation

HRID 465927 reaction equation
S(=O)(=O)(O)O.[C:6]([OH:17])(=[O:16])[C:7]1[CH:15]=[C:13]([OH:14])[C:11]([OH:12])=[C:9]([OH:10])[CH:8]=1.[CH3:18]O>>[C:6]([O:17][CH3:18])(=[O:16])[C:7]1[CH:15]=[C:13]([OH:14])[C:11]([OH:12])=[C:9]([OH:10])[CH:8]=1

Participants

4

Reactant 3

HCID 370Gallic AcidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 7428Methyl GallateYield 82%

Conditions

Temperature
10 °C

Procedure

Twenty 20 ml of concentrated sulfuric acid was added dropwise to a solution of 200 g of gallic acid in 600 ml of methanol at room temperature with stirring for 6-8 hours. After approximately 2/3 of the methanol was removed, the residue was cooled to 10° C., poured into 1.2 kg of water and allowed to stand overnight. The white precipitate which formed was filtered and washed with water to give 178 g of product methyl gallate, m.p. 200°-204° C. (yield 82%).

Workup

  1. customAfter approximately 2/3 of the methanol was removed
  2. additionpoured into 1.2 kg of water
  3. waitto stand overnight
  4. customThe white precipitate which formed
  5. filtrationwas filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-b68bfad313b942bab29dc4083c2202ba
Source dataset
uspto-grants-1992_10
Patent number
US05155111

Reaction notes

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