Reaction #54190

Reaction equation

tributylamine

acrolein

acrolein

diethyl bromomalonate

tributylamine

ethanol

→

yellow oil

γ,γ-dicarbethoxybutyraldehyde

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperaturewhile cooling in an ice bath
2. 2
   workup.WAITThe stirring was continued for an additional 1 to 2 hours without additional cooling
3. 3
   Otherthe ethanol and unreacted acrolein were removed on a rotary evaporator
4. 4
   workup.ADDITIONThe residue was diluted with 500 ml benzene
5. 5
   Washwashed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution
6. 6
   Otherrotary evaporated

Procedure

First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution. The benzene solution was dired over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc.

Source