Réaction #2006416

Équation de réaction

Sodium methoxide

4-carboxybenzaldehyde

acetophenone

→

43

Rendement 72.0%

4-(3-oxo-3-Phenylpropenyl)-benzoic Acid

Rendement 72.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Autrehalf of the volume of methanol was removed under reduced pressure
2. 2
   workup.ADDITIONThe mixture was poured into HCl 1M (50 mL) (until pH=2) and ethyl acetate
3. 3
   workup.ADDITIONwas added
4. 4
   ExtractionThe separated aqueous layer was extracted with ethyl acetate (3×30 mL)
5. 5
   Séchagedried (MgSO4 anh.)
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated
8. 8
   AutreThe residue was triturated with dichloromethane-hexanes (1:1)

Mode opératoire

Sodium methoxide (1.8 g, 33.3 mmol) was added to a stirred suspension of 4-carboxybenzaldehyde (2.5 g, 16.6 mmol) and acetophenone (2.0 g uL, 16.6 mmol) in methanol (50 mL) at room temperature. The mixture was stirred at room temperature for 16 hours, and half of the volume of methanol was removed under reduced pressure. The mixture was poured into HCl 1M (50 mL) (until pH=2) and ethyl acetate was added. The separated aqueous layer was extracted with ethyl acetate (3×30 mL) dried (MgSO4 anh.), filtered and evaporated. The residue was triturated with dichloromethane-hexanes (1:1) to afford 3 g of 43 (72% yield).

Source