Potassium Hydroxide → 3-Chloro-4-cyclohexylpropiolic acid

HRID 261589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 261589
Br[CH:2]([CH:8](Br)[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[Cl:15])[C:3]([O:5]CC)=[O:4].[OH-].[K+]>>[Cl:15][CH:10]1[CH:9]([C:8]#[C:2][C:3]([OH:5])=[O:4])[CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

3

Edukt 2

HCID 14797Potassium HydroxideHCID 57052243Ethyl alpha,beta-dibromo-beta-(3-chloro-4-cyclohexyl)propionate

Produkt 1

HCID 705420153-Chloro-4-cyclohexylpropiolic acid

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureThe mixture is refluxed on a steam bath for 6 hours
  2. customThe alcohol is evaporated
  3. dissolutionthe residue is dissolved in water
  4. washThe ether layer is washed with water, saline
  5. dry with materialdried over sodium sulfate
  6. customThe ether is removed
  7. customto give a residue which
  8. customis triturated with carbon tetrachloride
  9. customRecrystallization
  10. customtriturated with boiling carbon tetrachloride

Quellen und Nachweise

ORD-Eintrag
ord-0b19a350062c4f358df6b9a30136811a
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04166133

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