Hydrazine → beta-(p-Chlorophenyl)propionic acid

HRID 5024

Reaction equation

HRID 5024 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.NN>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 153712-Propenoic acid, 3-(4-chlorophenyl)-

Product 1

HCID 123137beta-(p-Chlorophenyl)propionic acidYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.75 g of 4-chlorocinnamic acid and 0.3 g of CuSO4.5H2O dispersed in 50 ml of ethyl alcohol was stirred at room temperature for 10 minutes; and 23 ml of 95% hydrazine was added thereto. This reactant was stirred for 18 hours with air bubbling at the speed of 1 L/min. The reaction mixture was filtered through a Celite layer and 30 ml of 1N NaOH was added thereto. The solution was washed twice with 30 ml of dichloromethane, acidified with concentrated hydrochloric acid, extracted with 100 ml of ethyl acetate four times and dried over magnesium sulfate. The solvent was evaporated to give 6.05 g(yield 89%) of 3-(4-chlorophenyl)propanoic acid as a yellow solid.

Workup

  1. stirringThis reactant was stirred for 18 hours with air
  2. custombubbling at the speed of 1 L/min
  3. filtrationThe reaction mixture was filtered through a Celite layer and 30 ml of 1N NaOH
  4. additionwas added
  5. washThe solution was washed twice with 30 ml of dichloromethane
  6. extractionextracted with 100 ml of ethyl acetate four times
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-161f70f75d474c90b1197e7470e29948
Source dataset
uspto-grants-1993_09
Patent number
US05242944

Linked notes

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