Hydrochloric Acid → 2'-Hydroxy-4'-iodo-3,4,5-trimethoxy-chalcone

Participants

Reaction Steps

To a stirring suspension of 29 (0.55 g, 2.1 mmol) and 3,4,5-trimethoxy-benzaldehyde (0.66 g, 3.4 mmol, 1.6 equ) in ethanol (10 ml) was added potassium hydroxide (0.25 g, 4.5 mmol, 2.1 equ). The reaction mixture was stirred for 119 hours then diluted with water, acidified (1N HCl) and extracted with ethyl acetate (3×70 ml). The combined organic layers were then washed with saturated aqueous sodium bicarbonate (50 ml), saturated brine (50 ml), 10% sodium bisulfite solution (3×50 ml) and then saturated brine (50 ml) again. The organic layer was then dried (MgSO4) and concentrated in vacuo to give a yellow solid (1.17 g). This solid was heated in methanol, and the undissolved solid collected. The filtrate was concentrated and then heated in methanol again. More undissolved solid was collected. Undissolved solid is 32 (0.50 g, 54%).

Provenance & Evidence