Acetophenone → 4-Carboxychalcone

HRID 916500Notes

Reaction equation

HRID 916500 reaction equation
C[O-].[Na+].[C:4]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)([OH:6])=[O:5].[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[CH3:16]>CO>[O:17]=[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:16]=[CH:11][C:10]1[CH:13]=[CH:14][C:7]([C:4]([OH:6])=[O:5])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 120884-Formylbenzoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 39957814-CarboxychalconeYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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).

Workup

  1. customhalf of the volume of methanol was removed under reduced pressure
  2. additionThe mixture was poured into HCl 1M (50 mL) (until pH=2) and ethyl acetate
  3. additionwas added
  4. extractionThe separated aqueous layer was extracted with ethyl acetate (3×30 mL)
  5. dry with materialdried (MgSO4 anh.)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was triturated with dichloromethane-hexanes (1:1)

Sources & evidence

ORD record
ord-9b7f120337104af7adc30a9e3a7e548f
Source dataset
uspto-grants-2007_09
Patent number
USRE039850E1

Reaction notes

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