Réaction #1679

Équation de réaction

3-(3-chlorobenzoyl)propionic acid

potassium hydroxide

hydrazine

→

product

Rendement 90.8%

4-(3-chlorophenyl)-butyric acid

Rendement 90.8%

Solvants

diethyleneglycol

Conditions de réaction

Traitement

1. 1
   AutreTo a 300 ml round-bottomed flask equipped with magnetic stirrer
2. 2
   Températurereflux condenser
3. 3
   TempératureThe mixture was heated
4. 4
   Autrewas azeotroped off into a Dean-Stark trap
5. 5
   TempératureThe reaction was refluxed for an additional 2 hours
6. 6
   Températurecooled
7. 7
   workup.ADDITIONpoured into 500 g of ice with 50 ml of con
8. 8
   AutreA white precipitate was formed which
9. 9
   Extractionwas extracted into 400 ml of ethyl ether
10. 10
    Lavagewashed with 100 ml of water and 100 ml of saturated sodium chloride solution
11. 11
    ExtractionThe ether extract
12. 12
    Séchagewas dried over anhydrous magnesium sulfate
13. 13
    Filtrationfiltered

Mode opératoire

To a 300 ml round-bottomed flask equipped with magnetic stirrer and reflux condenser was charged 23.7 g of 87% potassium hydroxide and 150 ml of diethyleneglycol, With stirring, 23 g of 3-(3-chlorobenzoyl)propionic acid was added followed by 24 g of 85% hydrazine. The mixture was heated to reflux for 2 hours when 50 ml of solvent was azeotroped off into a Dean-Stark trap. The reaction was refluxed for an additional 2 hours, cooled, and poured into 500 g of ice with 50 ml of con. hydrochloric acid. A white precipitate was formed which was extracted into 400 ml of ethyl ether, and washed with 100 ml of water and 100 ml of saturated sodium chloride solution. The ether extract was dried over anhydrous magnesium sulfate, filtered, and stripped to yield 19.5 g of product as a white solid.

Source