Reaktion #530085

Reaktionsgleichung

N-(3-Benzyloxy-5-methylphenyl)-2-hydroxy-2-methylpropanamide

NaOH

ethanol

→

title compound

Ausbeute 62.1%

3-Benzyloxy-5-methylaniline

Ausbeute 62.1%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 2 days
2. 2
   Extraktionextracted with dichloromethane (3×60 mL)
3. 3
   WaschenThe dichloromethane solution was washed with brine (2×50 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   SonstigeAfter evaporating the solvent in vacuo
6. 6
   Sonstigethe residue was purified by flash column chromatography (dichloromethane)

Vorschrift

N-(3-Benzyloxy-5-methylphenyl)-2-hydroxy-2-methylpropanamide (600 mg, 2.0 mmol), as prepared in the preceding step, was mixed with 10N NaOH (25 mL) and ethanol (10 mL), and the mixture was refluxed for 2 days. After cooling to ambient temperature, the mixture was diluted with water (60 mL) and extracted with dichloromethane (3×60 mL). The dichloromethane solution was washed with brine (2×50 mL) and dried over Na2SO4. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane) to give the title compound as a yellow oil (265 mg, 61%). 1H-NMR (300 MHz, CDCl3) δ 7.37 (m, 5 H), 6.24 (s, 1 H), 6.14 (s, 2 H), 5.00 (s, 2 H), 3.59 (br s, 2 H), 2.23 (s, 3 H).

Quelle