Water → HCID 19429479, compound

HRID 1078416Notes

Reaction equation

HRID 1078416 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:13][CH3:14])([CH2:11][CH3:12])[C:9]#[N:10])=[CH:4][CH:3]=1.[OH-:15].[K+].O>C(O)CCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH2:13][CH3:14])([CH2:11][CH3:12])[C:9]([NH2:10])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 19429486HCID 19429486, compound

Product 1

HCID 19429479HCID 19429479, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

2-(4-Chlorophenyl)-2-ethylbutyronitrile (104.9 g) was added to a boiling solution of potassium hydroxide (40.3 g) in pentan-1-ol (450 ml) with stirring. The mixture was boiled under reflux for 24 hours. The mixture was cooled and poured into an equal volume of water. The mixture was washed with ether and then the aqueous layer was extracted with dichloromethane to give an oil which solidified on standing. The solid was triturated with cyclohexane and filtered to give 2-(4-chlorophenyl)-2-ethylbutyramide, m.p. 107°-109° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureThe mixture was cooled
  3. washThe mixture was washed with ether
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. customto give an oil which
  6. customThe solid was triturated with cyclohexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-161a2f6e71424833967474d1d7484dec
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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