Hydrochloric Acid → 2'-Hydroxy-4',6'-dimethoxy-4-(methoxymethoxy)chalcone

Participants

Reaction Steps

To a stirred solution containing 1.57 g (8 m moles) of 2'-hydroxy-4',6'-dimethoxyacetophenone and 1.33 g (8 m moles) of 4-(methoxymethoxy)benzaldehyde in 3 ml of ethanol, there were added 30 ml of 15% by volume aqueous sodium hydroxide. After being stirred at room temperature for 2 days, the mixture was poured into 70 ml of ice-water. The pH was adjusted to 7 by adding hydrochloric acid, and the mixture was extracted with two 150 ml portions of dichloromethane. The combined extracts were washed with water, dried over sodium sulfate and then evaporated. The oily residue was crystallized from methanol to yield 780 mg of 2'-hydroxy-4',6'-dimethoxy-4-(methoxymethoxy)chalcone as yellow needles: mp 104.5° C.

Provenance & Evidence