Toluene → HCID 8033815, compound

Participants

Reaction Steps

In 150 ml of methylene chloride were dissolved 35.0 g of toluene and 22.4 g of itaconic anhydride. To this was added gradually 50.0 g of anhydrous aluminum chloride under ice-cooling with stirring, and then the mixture was stirred at room temperature for 5 hours for proceeding the reaction. After completion of the reaction, the reaction solution was concentrated under reduced pressure, poured into a mixture of 40 ml of conc. hydrochloric acid and 500 g of ice, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was evaporated and the residue was recrystallized from a mixture of hexane and ethyl acetate to give 21.6 g of 3-(4-methylbenzoyl)-2-methylenepropionic acid (a compound of formula II wherein X is CH3 and Y is H) (yield: 53%)

Provenance & Evidence