Sodium Hydroxide → Ethyl 2-benzylacrylate

HRID 1590761Notes

Reaction equation

HRID 1590761 reaction equation
[CH2:1]([CH:8]([C:14](OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([C:8](=[CH2:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69090Diethyl 2-benzylpropanedioate

Product 1

HCID 11084648Ethyl 2-benzylacrylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

127.6 g of diethyl 2-benzylmalonate are refluxed with 20.4 g of NaOH in 1 l of dry ethanol. After 8 hours, the solvent is removed, the residue is taken up in 2N HCl, and the solution is extracted with ether. The organic phase is dried and concentrated. The residue is cooled, and 51.2 ml of diethylamine and 43.7 ml of 36% strength formaldehyde solution are added. The mixture is left to stand overnight and then extracted with ether, and the extracts are dried and concentrated. The product is distilled.

Workup

  1. customthe solvent is removed
  2. extractionthe solution is extracted with ether
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. temperatureThe residue is cooled
  6. addition51.2 ml of diethylamine and 43.7 ml of 36% strength formaldehyde solution are added
  7. waitThe mixture is left
  8. waitto stand overnight
  9. extractionextracted with ether
  10. customthe extracts are dried
  11. concentrationconcentrated
  12. distillationThe product is distilled

Sources & evidence

ORD record
ord-d0d113a208b94d9c906e140bedf1cbda
Source dataset
uspto-grants-1993_04
Patent number
US05204357

Reaction notes

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