Acetophenone → 4-Carboxychalcone

HRID 1264351Notes

Reaction equation

HRID 1264351 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-6b3f84be913a485bbecf6d69eb39b586
Source dataset
uspto-grants-2003_04
Patent number
US06541661B1

Reaction notes

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