Potassium Hydroxide → 3-Chloro-4-cyclohexylpropiolic acid

HRID 839088Notes

Reaction equation

HRID 839088 reaction equation
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

Participants

3

Reactant 2

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

Product 1

HCID 705420153-Chloro-4-cyclohexylpropiolic acid

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.

Workup

  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

Sources & evidence

ORD record
ord-4da54ec2b206446cb4b9edba96d22ac2
Source dataset
uspto-grants-1978_06
Patent number
US04093737

Reaction notes

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