Abstract
Abstract The treatment of acetylacetone (I) with n-butyryl chloride in the presence of aluminum chloride in nitrobenzene gave n-butyrylacetone and di-n-butyrylmethane at 45°C. The same products were obtained, along with n-butyric acid, when n-butyrylacetone or di-n-butyrylmethane was treated with acetyl chloride under analogous conditions. The reactions between I and benzoyl chloride and between benzoylacetone or dibenzoylmethane and acetyl chloride gave products consisting of I, benzoylacetone, dibenzoyl-, diacetylbenzoyl-, acetyldibenzoyl-, tribenzoyl-methane, and benzoic acid. These findings show that β-diketone can reversibly react with acyl chloride to form new β-diketones by way of the mixed triacylmethanes. The acylation mechanism is discussed.
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