Reaction #5720

Reaction equation

methyl acetoacetate

ethyl bromide

sodium methylate

→

methyl 2-acetylbutyrate

Yield 56.9%

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureat reflux
2. 2
   workup.DISTILLATIONAfter distillation of the methanol the residue
3. 3
   workup.ADDITIONwas poured on to ice-water
4. 4
   ExtractionIt was then extracted with n-hexane and water
5. 5
   Otherdried
6. 6
   OtherAfter evaporation of the solvent
7. 7
   workup.DISTILLATIONdistillation there

Procedure

465 g of methyl acetoacetate and then 458 g of ethyl bromide were added under nitrogen to 720 g of 30% sodium methylate solution in 1200 ml of methanol. The reaction mixture was subsequently boiled at reflux. After distillation of the methanol the residue was poured on to ice-water. It was then extracted with n-hexane and water. The organic phases were combined and dried. After evaporation of the solvent and distillation there were obtained 328 g (56.9%) of methyl 2-acetylbutyrate, b.p. 77°-79°/15 Torr.

Source