Diethyl Malonate → 3-(2-Chlorophenyl)propanoic acid

HRID 1169166Notes

Reaction equation

HRID 1169166 reaction equation
[O-]CC.[Na+].[C:5](OCC)(=O)[CH2:6][C:7]([O:9]CC)=[O:8].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1CCl.[OH-].[K+]>C(O)C>[C:7]([CH2:6][CH2:5][C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[Cl:16])([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 119062-Chlorobenzyl chlorideHCID 14797Potassium HydroxideHCID 2723922Sodium ethoxide

Product 1

HCID 956763-(2-Chlorophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 171.0 g (2.51 mol) of sodium ethoxide in ethanol is admixed with 149.2 g (932 mmol) of diethyl malonate. 50.0 g (311 mmol) of 2-chlorobenzyl chloride are added to this reaction mixture, and after the addition is complete the reaction mixture is refluxed for three hours. After cooling to room temperature, 480 g (1.71 mol) of a KOH solution are added and the mixture is subsequently refluxed for another hour. The ethanol is then distilled off and the residue is subjected to an aqueous work-up and extracted three times with 100 ml each time of diethyl ether. The organic phase is discarded and the aqueous phase is brought to a pH of 1 using concentrated HCl. The mixture is subsequently extracted three times with 100 ml each time of diethyl ether. The combined organic phases are washed with 100 ml of water and then with 100 ml of a saturated NaCl solution.

Workup

  1. additionafter the addition
  2. temperatureis refluxed for three hours
  3. temperaturethe mixture is subsequently refluxed for another hour
  4. distillationThe ethanol is then distilled off
  5. extractionextracted three times with 100 ml each time of diethyl ether
  6. extractionThe mixture is subsequently extracted three times with 100 ml each time of diethyl ether
  7. washThe combined organic phases are washed with 100 ml of water

Sources & evidence

ORD record
ord-324d2b3103514eb58c288aa533fd3326
Source dataset
uspto-grants-2003_09
Patent number
US06627764B1

Reaction notes

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