Sulfuric Acid → Genistein

Participants

Reaction Conditions

Reaction Steps

To 159.8 g of anhydrous sodium carbonate (1.5 mol) in 950 ml of dimethylformamide were added 99.6 g of anhydrous phloroacetophenone (375 mmol) and the resulting yellow suspension was stirred for 3 hours under argon at 25° C., then cooled to 0° C. To this suspension was added the above solution of sodium formylsulfate within 2 minutes and the reaction mixture was stirred for 18 hours at 0° C., heated to 80° C., and held at that temperature during 30 minutes. To the hot mixture were added within 40 minutes 732 ml of sulfuric acid (36%). After gas evolution had ceased, 2.44 l water-dimethylformamide was distilled off at 80° C. and 15 mbar. To the thick suspension were added within 1.5 hours at 70° C. 3.99 l of hot water (50° C.). The white suspension was stirred and cooled to 20° C. overnight, then filtered. The filter cake was washed 3 times with 272 ml of water, then dried at 60° C. at 12 mbar overnight to yield 101.9 g of genistein as a light beige solid. The calculated yield was 95% (purity 93%, w/w, HPLC).

Provenance & Evidence