Reaction #2006416

Reaction equation

Sodium methoxide

4-carboxybenzaldehyde

acetophenone

→

43

Yield 72.0%

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

Yield 72.0%

Solvents

methanol

Conditions

Workup

1. 1
   Otherhalf 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
   Dryingdried (MgSO4 anh.)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   OtherThe residue was triturated with dichloromethane-hexanes (1:1)

Procedure

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