Reaction #348771

Reaction equation

ethyl α,β-dibromo-β-(3-chloro-4-cyclohexyl)propionate

potassium hydroxide

→

3-chloro-4-cyclohexylpropiolic acid

Conditions

Workup

1. 1
   TemperatureThe mixture is refluxed on a steam bath for 6 hours
2. 2
   OtherThe alcohol is evaporated
3. 3
   workup.DISSOLUTIONthe residue is dissolved in water
4. 4
   WashThe ether layer is washed with water, saline
5. 5
   Dryingdried over sodium sulfate
6. 6
   OtherThe ether is removed
7. 7
   Otherto give a residue which
8. 8
   Otheris triturated with carbon tetrachloride
9. 9
   OtherRecrystallization
10. 10
    Othertriturated with boiling carbon tetrachloride

Procedure

Powdered ethyl α,β-dibromo-β-(3-chloro-4-cyclohexyl)propionate (33.0 g.) is added portion-wise to 20% ethanolic potassium hydroxide (135 ml) at room temperature. The mixture is refluxed on a steam bath for 6 hours. The alcohol is evaporated and the residue is dissolved in water and covered with ether and is acidified with cold, dilute hydrochloric acid. The ether layer is washed with water, saline, and dried over sodium sulfate. The ether is removed to give a residue which is triturated with carbon tetrachloride. Recrystallization is carried out from acetic acid-water. This material is digested and triturated with boiling carbon tetrachloride to give 3-chloro-4-cyclohexylpropiolic acid.

Source