Hydrochloric Acid → 3,4,5-Trihydroxybenzamide
Reaction equation
[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]=1Participants
16
Reactant 12
HCID 313Hydrochloric Acid
HCID 370Gallic Acid
HCID 6367Acetyl chloride
HCID 7918Acetic Anhydride
HCID 8471Triethylamine
HCID 10340Sodium Carbonate
HCID 14798Sodium Hydroxide2×
HCID 24386Thionyl Chloride
HCID 24387Phosphorus trichloride
HCID 95088Benzoic acid, 3,4,5-tris(acetyloxy)-
HCID 1555063,4,5-Triacetoxybenzoyl chloride
HCID 517045Sodium AcetateProduct 1
Reagents, catalysts & solvents 3
Procedure
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.
Sources & evidence
- ORD record
- ord-cdde5cb78ea24ee3b3a1e264077d2e68
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04476219
Reaction notes
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