Reaktion #83881

Reaktionsgleichung

1-[3-acetylamino-4-hydroxyphenyl] ethanone

K2CO3

3-chloro-1-bromopropane

→

white solid

Ausbeute 78.8%

1-[3-acetylamino-4-(3-chloropropoxy)phenyl]ethanone

Ausbeute 78.8%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 16 hours
2. 2
   Filtrationfiltered

Vorschrift

A stirred mixture of 1-[3-acetylamino-4-hydroxyphenyl] ethanone (7.7 g, 40 mmol), K2CO3 (5.7 g), 3-chloro-1-bromopropane (8.9 g, 56 mmol) and acetone (100 ml) was refluxed for 16 hours. The reaction was allowed to cool to ambient temperature and filtered. Concentration of the flitrate yielded 8.5 g of a white solid. The solid was recrystallized from toluene and then from ethanol to afford 6.5 g of an off-white solid. A 3.3 g sample of this material was flash chromatographed on silica gel with ethyl acetate as eluent. Concentration of the appropriate fractions afforded 2.8 g of a solid. The solid was recrystallized from toluene and then from ethanol-water to yield 2.2 g (51%) of a solid, m.p.=124°-126° C.

Quelle