Reaktion #50776

Reaktionsgleichung

2-chloroethanol

5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one

hydrochloric acid

→

5,7-di-tert-butyl-3-[4-(2-hydroxyethoxy)phenyl]-benzofuran-2-one

Ausbeute 61.2%

Lösungsmittel

sodium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is then maintained at 80° C. for 2 hours
2. 2
   Temperaturthe mixture is cooled
3. 3
   Extraktionthe product is extracted with dichloromethane
4. 4
   WaschenThe organic phases are washed with water
5. 5
   Trocknendried over sodium sulfate
6. 6
   Einengenconcentrated on a vacuum rotary evaporator
7. 7
   SonstigeCrystallization of the residue from 8 ml of ethanol and 2 ml of water

Vorschrift

1.0 ml (15.0 mmol) of 2-chloroethanol is added to a solution of 3.38 g (10.0 mmol) of 5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one in 30 ml of 1N sodium hydroxide solution heated to 80° C. The reaction mixture is then maintained at 80° C. for 2 hours, 50 ml of 1N hydrochloric acid are added, stirring is continued for 1 hour, the mixture is cooled, and the product is extracted with dichloromethane. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallization of the residue from 8 ml of ethanol and 2 ml of water gives 2.34 g (61%) of 5,7-di-tert-butyl-3-[4-(2-hydroxyethoxy)phenyl]-benzofuran-2-one m.p. 132°-135° C. (compound (105), Table 1).

Quelle