Benzoyl chloride → Methyl 6-chloro-3-methylflavone-8-carboxylate

Participants

Reaction Steps

A 23.8 g (0.165 mole) quantity of sodium benzoate was added with stirring to a mixture of 12.1 g (0.05 mole) of methyl 5-chloro-3-propionylsalicylate and 21.1 g (0.15 mole) of benzoyl chloride. The resulting mixture was heated at 180° to 190° C. in an oil bath for 8 hours to undergo reaction. After cooling, 100 ml of a 5% aqueous solution of sodium carbonate was added to the reaction mixture and the admixture was stirred. The solids formed were recrystallized from alcohol, giving 14.8 g (90.1%) of white crystal, which was repeatedly recrystallized from alcohol to obtain a compound having a melting point of 171.5° to 173.0° C. The compound was chemically analyzed with the results shown in Table 1 given below.

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