تفاعل #2006416

ord-479347c73df04b7e86de16f02bedb713

معادلة التفاعل

C[O-].[Na+]
Sodium methoxide
O=Cc1ccc(C(=O)O)cc1
4-carboxybenzaldehyde
CC(=O)c1ccccc1
acetophenone
O=C(O)c1ccc(C=CC(=O)c2ccccc2)cc1
43
المردود 72.0%
O=C(O)c1ccc(C=CC(=O)c2ccccc2)cc1
4-(3-oxo-3-Phenylpropenyl)-benzoic Acid
المردود 72.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىhalf 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
    استخلاصThe separated aqueous layer was extracted with ethyl acetate (3×30 mL)
  5. 5
    تجفيفdried (MgSO4 anh.)
  6. 6
    ترشيحfiltered
  7. 7
    أخرىevaporated
  8. 8
    أخرىThe residue was triturated with dichloromethane-hexanes (1:1)

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: USRE043343E1uspto-grants-2012_05