Reaktion #2348130

Reaktionsgleichung

4-Hydroxybenzoic acid

4-aminophenol

EDCI

→

4-hydroxy-N-(4-hydroxyphenyl)-benzamide

Ausbeute 34.6%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was then partitioned between EtOAc (200 mL) and water (200 mL)
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed consecutively with 1 N HCl, water, saturated sodium bicarbonate solution, water, and brine
4. 4
   Trocknendried over MgSO4
5. 5
   SonstigeSolvent was removed under reduced pressure
6. 6
   Sonstigethe crude product was purified by column chromatography

Vorschrift

4-Hydroxybenzoic acid (1.01 g, 7.31 mmol) and 4-aminophenol (1.19 g, 10.9 mmol) were dissolved in 15 mL of dry DMF. To the above solution EDCI (1.40 g, 7.31 mmoL) was added in one portion and the resulting mixture was stirred at rt overnight under nitrogen. The reaction mixture was then partitioned between EtOAc (200 mL) and water (200 mL). The organic layer was separated, washed consecutively with 1 N HCl, water, saturated sodium bicarbonate solution, water, and brine, and dried over MgSO4. Solvent was removed under reduced pressure and the crude product was purified by column chromatography using EtOAc in hexane as an eluent (10% to 20%) to give 580 mg (34% yield) of 4-hydroxy-N-(4-hydroxyphenyl)-benzamide. MS (ES) m/z: 230.04 (M+1).

Quelle