Gallic Acid → Benzoic acid, 3,4,5-tris(acetyloxy)-

HRID 1632279Notes

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.C(O[C:17](=[O:19])[CH3:18])(=O)C.[C:20](Cl)(=[O:22])[CH3:21].[OH-].[Na+].[C:26]([O-:29])([O-])=O.[Na+].[Na+].N1C=CC=C[CH:33]=1>>[C:20]([O:5][C:4]1[CH:3]=[C:2]([CH:10]=[C:8]([O:9][C:17](=[O:19])[CH3:18])[C:6]=1[O:7][C:26](=[O:29])[CH3:33])[C:1]([OH:12])=[O:11])(=[O:22])[CH3:21]

Participants

Reactant 6

HCID 370Gallic Acid

HCID 1049Pyridine

HCID 6367Acetyl chloride

HCID 7918Acetic Anhydride

HCID 10340Sodium Carbonate

HCID 14798Sodium Hydroxide

Product 1

HCID 95088Benzoic acid, 3,4,5-tris(acetyloxy)-

Procedure

Gallic acid is reacted with acetic anhydride or acetic chloride in the presence of bases, such as NaOH (J. Chem. Soc., 2495 (1931)), Na2CO3, or pyridine, to form 3,4,5-triacetoxybenzoic acid, which is then treated with thionyl chloride or phosphorus trichloride to form the corresponding acid chloride. This 3,4,5-triacetoxybenzoic acid chloride is reacted with a suitable amine compound in the presence of bases, such as pyridine and triethylamine, and thereafter, treated with sodium acetate, sodium hydroxide, hydrochloric acid or the like in methanol or ethanol to form the desired gallic acid amide.

Sources & evidence

ORD record: ord-44724885dbf34238a40fac2f03e152cc
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04474874

Reaction notes

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