Reaction #2006417

Reaction equation

4-carbomethoxybenzaldehyde

acetophenone

sodium methoxide

HCl

→

Methyl-4-(3-oxo-3-phenylpropenyl)-benzoate

Solvents

methanol

EtOAc

Conditions

Workup

1. 1
   Temperaturethen heated
2. 2
   Temperatureto reflux for 1 hour
3. 3
   Temperaturecooled down to room temperature
4. 4
   OtherThe layers were separated
5. 5
   Dryingthe organic layer dried over anhydrous MgSO4
6. 6
   Filtrationfiltered
7. 7
   OtherThe solvent was evaporated under vacuum
8. 8
   Otherto afford a yellow solid, which
9. 9
   Otherwas recrystallized from acetonitrile/water
10. 10
    Otherto give a pale yellow crystalline solid

Procedure

To 4-carbomethoxybenzaldehyde (79 mg, 0.48 mmol) and acetophenone (56 μL, 0.48 mmol) in anhydrous methanol (1.6 mL), was added neat sodium methoxide (26 mg, 0.48 mmol). The mixture was stirred at room temperature overnight then heated to reflux for 1 hour, cooled down to room temperature and added HCl 1N and EtOAc. The layers were separated and the organic layer dried over anhydrous MgSO4 and filtered. The solvent was evaporated under vacuum to afford a yellow solid, which was recrystallized from acetonitrile/water to give a pale yellow crystalline solid.

Source