Ethanol → HCID 18986860, compound

HRID 2397062Notes

Reaction equation

HRID 2397062 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([CH2:10][CH2:11]CC#N)[CH:9]=1.[CH2:24]([OH:26])[CH3:25]>>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([CH2:10][CH2:11][CH2:25][C:24]([OH:1])=[O:26])[CH:9]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 18986921HCID 18986921, compound

Product 1

HCID 18986860HCID 18986860, compound

Procedure

15 ml of a 20% (w/v) aqueous solution of potassium hydroxide was added to a solution of 1.53 g of the crude 4-[5-chloro-2-(2-phenylethoxy)phenyl]butyronitrile in 15 ml of ethanol and the resulting mixture was heated under reflux for 17 hours. After evaporation of the ethanol under reduced pressure, conc. hydrochloric acid was added dropwise to the reaction mixture until it became acidic. Then the reaction mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 1.41 g of crude 4-[5-chloro-2-(2-phenylethoxy)phenyl]butyric acid was obtained. This compound was not purified any more but used in the subsequent reaction.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 17 hours
  3. customAfter evaporation of the ethanol under reduced pressure, conc. hydrochloric acid
  4. additionwas added dropwise to the reaction mixture until it
  5. extractionThen the reaction mixture was extracted with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4091d0ffd1a14873bae040f3283066de
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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