HCID 10473458, compound → HCID 19878336, compound

Participants

Reaction Steps

A 15 g portion of 4-(4-hydroxybenzoyl)-3-(4-methoxyphenyl)-1,2-dihydronaphthalene was dissolved in 200 g of methanesulfonic acid under nitrogen, and was stirred overnight at ambient temperature. Then the suspension was poured over 200 g of ice and the mixture was added to 100 ml of brine, which was in turn extracted with 300 ml of ethyl acetate. The organic extract was then washed with 100 ml of water, with 100 ml of saturated aqueous sodium bicarbonate solution, and again with 20 ml of brine. The organic extract was concentrated and the residue was digested with hot isopropanol. The digestion mixture was cooled overnight to obtain 3.2 g of the desired product. That product was recrystallized from ethyl acetate to obtain 2.74 g of the desired product in pure form. The product was identified by its field desorption mass spectrum m/e 338 (calc'd m/e 338) and its NMR spectrum.

Provenance & Evidence