Pyridine → (3-Acetamidophenyl) acetate

Reaktionsgleichung

[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10](OC(C)=O)=[O:11].N1[CH:21]=[CH:20]C=CC=1.C([O-])(O)=[O:23].[Na+]>>[C:10]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:20](=[O:23])[CH3:21])[CH:3]=1)(=[O:11])[CH3:9]

Komponenten

Edukt 4

HCID 1049Pyridine

HCID 7918Acetic Anhydride

HCID 115683-Aminophenol

HCID 516892Sodium Bicarbonate

Produkt 1

HCID 231988(3-Acetamidophenyl) acetateAusbeute 93 %

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

3-aminophenol (19 g, 17 mol) was dissolved in Ac2O (162 g, 1.59 mol, 9.5 eq.), and pyridine (4.9 g, 0.062 mol, 0.36 eq.) was added. Then the reaction mixture was stirred at 80° C. over 2 h. Ice water (50 mL) was added to the mixture, and added saturated NaHCO3 solution to the mixture until pH=7, then extracted (ethyl acetate), washed (brine), dried (Na2SO4), concentrated to give 3-acetamidophenyl acetate as gray solid (30 g, yield: 93%). ESI-MS: 194 (M+H)+.