2',4,4'-trihydroxychalcone synthesis
- Product Name:2',4,4'-trihydroxychalcone
- CAS Number:13745-20-5
- Molecular formula:C15H12O4
- Molecular Weight:256.25
Yield:13745-20-5 73.2%
Reaction Conditions:
Stage #1: 2',4'-dihydroxy-4-acetophenonewith potassium hydroxide in ethanol;water at 20; for 0.166667 h;Claisen-Schmidt Condensation;
Stage #2: 4-hydroxy-benzaldehyde in ethanol;water at 85; for 2 h;
Steps:
4.2.2 General synthetic procedure for compounds RY3-a (RY3-a-1-RY3-a-15)
General procedure: 2,4-Dihydroxyacetophenone derivatives (44.7mmol) in EtOH (20mL) were added to aqueous potassium hydroxide (41.6mL, 60% w/w) under magnetic stirring for 10min at room temperature followed by the addition of 2,3-dihydroxybenzaldehyde derivatives (45.9mmol). The mixture was stirred magnetically at 85 °C for 2h and then poured onto ice. The reaction mixture was acidified to a pH=4 using cold hydrochloric acid and extracted with EtOAc. The combined EtOAc extracts were washed with brine solution, dried with Na2SO4 and concentrated under reduced pressure. Purification of the crude product by flash chromatography (20% EtOAc/hexane) yielded RY3-a-1-RY3-a-15.
References:
Zhong, Hui;Zhou, Jia;An, Xiao-Hong;Hua, Ying-Rong;Lai, Yi-Fan;Zhang, Rui;Ahmad, Owais;Zhang, Ye;Shang, Jing [Bioorganic Chemistry,2019,vol. 87,p. 523 - 533]
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