Reaction #2941

Reaction equation

ethyl acetoacetate

i-butyl alcohol

p-toluensulphonic acid

→

title compound

i-Butyl acetoacetate

Conditions

Workup

1. 1
   TemperatureThe solution was refluxed for 18 h
2. 2
   OtherThe reaction mixture was evaporated in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ether
4. 4
   workup.ADDITIONThe resulted solution was treated with s.s
5. 5
   OtherThe organic layer was separated
6. 6
   Dryingdried over Na2SO4
7. 7
   Otherevaporated in vacuo
8. 8
   workup.DISTILLATIONThe crude oil was distilled at 66°-68° C./4 mmHg

Procedure

30 ml of ethyl acetoacetate were dissolved in 350 ml of i-butyl alcohol and a catalytic amount of p-toluensulphonic acid (PTSA) was added. The solution was refluxed for 18 h. The reaction mixture was evaporated in vacuo and the residue was dissolved in ether. The resulted solution was treated with s.s. NaHCO3. The organic layer was separated, dried over Na2SO4 and evaporated in vacuo. The crude oil was distilled at 66°-68° C./4 mmHg, to give 18.8 g of the title compound.

Source