ChemicalBook CAS DataBase List 2,4,4'-TRIHYDROXY BENZALACETOPHENONE

2,4,4'-TRIHYDROXY BENZALACETOPHENONE synthesis

5synthesis methods

Product Name:2,4,4'-TRIHYDROXY BENZALACETOPHENONE
CAS Number:83616-07-3
Molecular formula:C15H12O4
Molecular Weight:256.25

(E)-3-(2,4-dimethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

24533-49-1
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83616-07-3
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Yield:83616-07-3 78%

Reaction Conditions:

with boron tribromide in dichloromethane at 0 - 20; for 24 h;Inert atmosphere;

Steps:

3. Demethylation using BBr₃: General Procedure

General procedure: The correspondingmethoxy substituted chalcones (0.25 mmol) obtained from the previous step (1) were dissolved in dried CH₂Cl₂(15 mL) and cooled down to 0^oC. BBr₃ (2 equiv per anypotentially basic Nor O) was slowly added to the reaction mixture kept under N₂atmosphere. After stirring for 24h at room temperature, the reaction was cooledto 0^oC and quenched with a very slow addition of H₂O. Theresulting red solids were separated by filtration and washed with H₂Oand CH₂Cl₂. The crude product was further purified bycolumn chromatography over Si gel using 20% MeOH in CH₂Cl₂to afford the hydroxyl chalcones.

References:

Nijampatnam, Bhavitavya;Casals, Luke;Zheng, Ruowen;Wu, Hui;Velu, Sadanandan E. [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 15,p. 3508 - 3513] Location in patent:supporting information