1-Chloro-4-(chloromethyl)benzene → HCID 11460315, compound

HRID 1954479Notes

Reaction equation

HRID 1954479 reaction equation
[O-]CC.[Na+].[C:5]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][CH:18]=1>C(O)C>[CH2:14]([O:13][C:5](=[O:12])[CH:6]([CH2:23][C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:15]

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxide

Product 1

HCID 11460315HCID 11460315, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

60.17 g of sodium ethoxide were dissolved in 1127 ml of ethanol. To this solution, 336.4 g of diethyl malonate and 115.0 g of (4-chlorophenyl) methyl chloride were added and the mixture was refluxed for 2 hours. After the reaction was completed, the solvent was removed under reduced pressure and water was added to the residue. After extraction with ethyl acetate, the ethyl acetate was dried with sodium sulfate anhydride. After removing the solvent under reduced pressure and purification with distillation, 172.6 g of 2-[(4-chlorophenyl)methyl]malonic acid diethyl ester were obtained.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customthe solvent was removed under reduced pressure and water
  3. additionwas added to the residue
  4. extractionAfter extraction with ethyl acetate
  5. dry with materialthe ethyl acetate was dried with sodium sulfate anhydride
  6. customAfter removing the solvent
  7. customunder reduced pressure and purification
  8. distillationwith distillation

Sources & evidence

ORD record
ord-1037ea7b792b497ebad7dd3a4b01ba55
Source dataset
uspto-grants-2000_09
Patent number
US06121477

Reaction notes

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