Cinnamoylbenzene → HCID 284115, compound

HRID 1525620Notes

Reaction equation

HRID 1525620 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:17][CH2:18]C(C1C=CC=CC=1)=O.C[O:28]C1C=CC(C=O)=CC=1.[OH-].[K+]>C(O)C>[OH:28][C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=1[CH:7]=[CH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 7189Cinnamoylbenzene2×HCID 14797Potassium HydroxideHCID 312444-MethoxybenzaldehydeHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 284115HCID 284115, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The synthesis of the chalcone compounds of the present invention was carried out by a Claisen-Schmidt condensation. Taking chalcone compound 1 as the example, a mixture of 2-hydroxyacetophenone (273.6 mg, 2.01 mmol), 4-methoxybenzaldehyde (279.1 mg, 2.05 mmol), potassium hydroxide (KOH, 50% w/v, 2 ml) and ethanol (100% v/v, 20 ml) was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure and then partitioned with ethyl acetate (EtOAc) and H2O. The organic layer was then evaporated, and the residue was purified using column chromatography (silica gel: 70-230, Merck; n-hexane-EtOAc, 15:1, Rf=0.2) to give 2-hydroxy-4′-methoxychalcone (chalcone compound 1, 273.6 mg; yield, 53.6%). The purity of compound 1 was greater than 95%, which was determined by high-performance liquid chromatography (HPLC).

Workup

  1. customwas carried out by a Claisen-Schmidt condensation
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned with ethyl acetate (EtOAc) and H2O
  4. customThe organic layer was then evaporated
  5. customthe residue was purified

Sources & evidence

ORD record
ord-f2b644889d60419fa7a945e7089f4a92
Source dataset
uspto-grants-2015_07
Patent number
US09085520B2

Reaction notes

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