3',4'-DIMETHOXY-2'-HYDROXYCHALCONE synthesis

Yield:32329-98-9 79%

Reaction Conditions:

Stage #1: 1-(2-hydroxy-4-methoxyphenyl)ethanonewith sodium hydroxide in methanol at 0; for 0.5 h;Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde in methanol;Inert atmosphere;

Steps:

The general method for the preparation of chalconesseries 1 and series 2

General procedure: Under N2 atmosphereand 0 ^OC, 1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone (1mmol, 1 eq) or1-(2-hydroxy-4,6-dimethoxyphenyl)propan-1-one (1mmol, 1 eq) was dissolved into10 ml MeOH, followed by the addition of 10 ml aq. 40% NaOH solution, themixture was stirred for about 30 min, then benzaldehydes (1.2 mmol, 1.2eq.)were added respectively. The mixture was stirred for overnight and monitored byTLC. After the starting material 1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone or 1-(2-hydroxy-4,6-dimethoxyphenyl)propan-1-onewas consumed completely, the pH value was adjusted to 3 with aq. 3 N HClsolution, a large amount of yellowish solid formed. The crude product was filtrated,recrystallized from MeOH or purified by si-gel column chromatography to affordfine desired products.

References:

Chen, Lijuan;Fan, Tiantian;Lei, Xiangui;Teichmann, Alexander Tobias;Wang, Amu;Wang, Chao;Wei, Zhe;Wieland, Frank Heinrich;Yang, Youzhe;Yin, Jinxiang;Zhou, Li;Zhu, Yue [European Journal of Medicinal Chemistry,2020,vol. 193] Location in patent:supporting information