Reaktion #75334

Reaktionsgleichung

8-hydroxyquinoline

3-chloropropionic acid

→

3-[8-quinolinoxy]-propionic acid

Ausbeute 25.0%

Lösungsmittel

potassium hydroxide

potassium hydroxide

potassium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added over 15 minutes
2. 2
   Temperaturthe subsequent 1.5 hour reflux period
3. 3
   TemperaturAfter cooling
4. 4
   Filtrationfiltration the mixture
5. 5
   Extraktionextracted with 6×100 ml chloroform
6. 6
   Sonstigethe precipitate thus formed
7. 7
   Filtrationwas filtered
8. 8
   Waschenwashed thoroughly with water

Vorschrift

A solution of 8-hydroxyquinoline (43.5 g, 0.30 mol) (Aldrich) in 150 ml 2 N potassium hydroxide was refluxed while an ice cold solution of 3-chloropropionic acid (36 g, 0.33 mol) (Aldrich) in 165 ml 2 N potassium hydroxide was added over 15 minutes. The pH of the reaction was maintained at pH 10 by addition of 5 N potassium hydroxide during the addition and the subsequent 1.5 hour reflux period. After cooling and filtration the mixture was brought to pH with 6 N hydrochloric acid and extracted with 6×100 ml chloroform. The aqueous layer was acidified to pH 3.8 with 6 N hydrochloric acid and the precipitate thus formed was filtered and washed thoroughly with water, to yield 3-[8-quinolinoxy]-propionic acid (16.12 g, 25% yield), m.p. 211°-213° C.

Quelle