Reaction #696703

Reaction equation

4-Vinylbenzyl chloride

Ethyl acetoacetate

sodium ethoxide

→

ethyl 2-(4-vinylbenzyl)-3-oxobutanoate

Yield 95.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewas cooled in an ice-water bath
2. 2
   TemperatureThe mixture was refluxed for 16 hours
3. 3
   Filtrationthe resulting slurry was filtered
4. 4
   Otherto remove any salt
5. 5
   Otherthe solution collected
6. 6
   OtherThe solvent was removed under reduced pressure

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.

Source