Reaction #1611

Reaction equation

3-(3-chlorobenzoyl)-propionic acid

potassium hydroxide

hydrazine

→

product

Yield 90.8%

4-(3-chlorophenyl)-butyric acid

Yield 90.8%

Solvents

diethyleneglycol

Conditions

Workup

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

Procedure

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