Sodium Chloride → Diethyl [(4-ethenylphenyl)methyl]propanedioate

HRID 1885951Notes

Reaction equation

HRID 1885951 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1)=[CH2:14].[Cl-].[Na+]>O.C(O)C>[CH:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[CH:17][CH:16]=1)=[CH2:14]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7761Diethyl MalonateHCID 74126p-Vinylbenzyl chlorideHCID 5360545Sodium

Product 1

HCID 13130740Diethyl [(4-ethenylphenyl)methyl]propanedioateYield 70.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Into a flask containing 100 ml of dry ethanol were fed 2.43 g (0.106 mole) of metallic sodium, 50.77 g (0.317 mole) of diethyl malonate and 16.12 g (0.106 mole) of p-vinylbenzyl chloride in dry nitrogen gas atmosphere. The mixture was subjected to reaction at the reflux temperature for 3 hours. 100 ml of pure water was added to the reaction mixture to dissolve the sodium chloride (NaCl) generated by the reaction. Extraction was carried out with three 100 ml-portions of methylene chloride to obtain a methylene chloride solution of the product, i.e., diethyl 2-(p-vinylbenzyl)malonate.

Workup

  1. customThe mixture was subjected to reaction at the reflux temperature for 3 hours
  2. customgenerated by the reaction
  3. extractionExtraction

Sources & evidence

ORD record
ord-bad9b30b5d214189af673f7c68d1c2a0
Source dataset
uspto-grants-1992_09
Patent number
US05147952

Reaction notes

Loading…