Diethyl Succinate → HCID 12918688, compound

HRID 1758890Notes

Reaction equation

HRID 1758890 reaction equation
[Na].[Cl:2][C:3]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:4]=1[CH2:5][C:6]#[N:7].[CH2:13]([O:15][C:16](=[O:24])[CH2:17][CH2:18][C:19](OCC)=[O:20])[CH3:14]>>[Cl:2][C:3]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:4]=1[CH:5]([C:6]#[N:7])[C:19](=[O:20])[CH2:18][CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:24]

Participants

4

Reactant 3

HCID 31249Diethyl SuccinateHCID 805662,4-DichlorophenylacetonitrileHCID 5360545Sodium2×

Product 1

HCID 12918688HCID 12918688, compoundYield 50%

Procedure

A clean, dry 500 ml 3-neck R.B. flask was equipped with a reflux condenser, mechanical stirrer, addition funnel, and nitrogen inlet. The flask was charged with 600 ml of ethanol (distilled from magnesium turnings and stored over type 3A molecular sieves) followed by 30.0 g (1.3 0 mol) of sodium, and the reaction mixture stirred and heated until all the sodium had dissolved. The temperature of the reaction mixture was then raised to the reflux point, and a mixture of 186.03 g (1.00 mol) of 2,4-dichlorobenzyl cyanide and 261.3 g (1.50 mol) of diethylsuccinate added at a rapid drop rate through the addition funnel. The reaction mixture was refluxed for 12 hours, then approximately 2/3 of the ethanol was distilled off, the reaction mixture refluxed for two additional hours, cooled to room temperature, and poured into 600 ml of ice water. The basic solution was extracted twice with 300 ml of ether, and then acidified with 6 N HCl. An oil formed, and the aqueous acid solution was extracted twice with 250 ml portions of ether. The ether extract was washed twice with water, dried (MgSO4), and the ether stripped to leave 156.61 g (50% yield) of product as a viscous red oil.

Workup

  1. customA clean, dry 500 ml 3-neck R.B
  2. customflask was equipped with a reflux condenser, mechanical stirrer, addition funnel, and nitrogen inlet
  3. additionThe flask was charged with 600 ml of ethanol (distilled from magnesium turnings and stored over type 3A molecular sieves)
  4. dissolutionhad dissolved
  5. temperatureThe temperature of the reaction mixture was then raised to the reflux point
  6. additionadded at a rapid drop rate through the addition funnel
  7. temperatureThe reaction mixture was refluxed for 12 hours
  8. distillationapproximately 2/3 of the ethanol was distilled off
  9. temperaturethe reaction mixture refluxed for two additional hours
  10. additionpoured into 600 ml of ice water
  11. extractionThe basic solution was extracted twice with 300 ml of ether
  12. customAn oil formed
  13. extractionthe aqueous acid solution was extracted twice with 250 ml portions of ether
  14. extractionThe ether extract
  15. washwas washed twice with water
  16. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-ace618a8b52846ecb796ee57304b255f
Source dataset
uspto-grants-1982_07
Patent number
US04338122

Reaction notes

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