Hydrochloric Acid → 3,4,5-Trihydroxybenzamide

HRID 1632639

Reaktionsgleichung

Reaktionsgleichung von HRID 1632639
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.C(OC1C=C(C=C(OC(=O)C)C=1OC(=O)C)C(O)=O)(=O)C.C(OC(=O)C)(=O)C.C(Cl)(=O)C.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+].S(Cl)(Cl)=O.P(Cl)(Cl)Cl.C(OC1C=C(C=C(OC(=O)C)C=1OC(=O)C)C(Cl)=O)(=O)C.C([O-])(=O)C.[Na+].Cl.C([N:90](CC)CC)C>CO.C(O)C.N1C=CC=CC=1>[C:1]([NH2:90])(=[O:12])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1

Komponenten

16

Edukt 12

HCID 313Hydrochloric AcidHCID 370Gallic AcidHCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide2×HCID 24386Thionyl ChlorideHCID 24387Phosphorus trichlorideHCID 95088Benzoic acid, 3,4,5-tris(acetyloxy)-HCID 1555063,4,5-Triacetoxybenzoyl chlorideHCID 517045Sodium Acetate

Produkt 1

HCID 692563,4,5-Trihydroxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

Namely, gallic acid is converted into 3,4,5-triacetoxybenzoic acid by reacting with acetic anhydride or acetic acid chloride in the presence of a base such as NaOH (J. Chem. Soc., 2495 (1931)), Na2CO3, pyridine or so on and, further, converted into the corresponding acid chloride by reacting with thionyl chloride or phosphorus trichloride. The thus-obtained 3,4,5-triacetoxybenzoic acid chloride was made to react with an appropriate amine in the presence of a base such as pyridine, triethylamine or the like. Thereafter, the reaction product is treated with sodium acetate, sodium hydroxide or hydrochloric acid in methanol or ethanol to produce an intended gallic acid amide.

Quellen und Nachweise

ORD-Eintrag
ord-cdde5cb78ea24ee3b3a1e264077d2e68
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04476219

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