Ethyl Acetoacetate → HCID 19599015, compound

HRID 609521Notes

Reaction equation

HRID 609521 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[O-]CC.[Na+].[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1)=[CH2:15]>C(O)C>[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][CH:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:18][CH:17]=1)=[CH2:15]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 74126p-Vinylbenzyl chlorideHCID 2723922Sodium ethoxide

Product 1

HCID 19599015HCID 19599015, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl acetoacetate (27.61 g, 0.21 mol) was dissolved in ethanol (100 ml) which was cooled in an ice-water bath, and sodium ethoxide (15.59 g, 0.22 mol) was added. 4-Vinylbenzyl chloride (33.92 g, 0.2 mole) was added. The mixture was refluxed for 16 hours, then the resulting slurry was filtered to remove any salt, and the solution collected. The solvent was removed under reduced pressure to give ethyl 2-(4-vinylbenzyl)-3-oxobutanoate in the form of a light red liquid (49 g) in 95% yield.

Workup

  1. temperaturewas cooled in an ice-water bath
  2. temperatureThe mixture was refluxed for 16 hours
  3. filtrationthe resulting slurry was filtered
  4. customto remove any salt
  5. customthe solution collected
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2068622bef2e4f6bb930d7ee2f308d0b
Source dataset
uspto-grants-1999_12
Patent number
US05998092

Reaction notes

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