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

HRID 1632279

Reaktionsgleichung

Reaktionsgleichung von HRID 1632279
[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]

Komponenten

7

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-44724885dbf34238a40fac2f03e152cc
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04474874

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