Sulfuric Acid → 3-(2,4-Dichlorobenzoyl)pentane-2,4-dione

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Reaction Steps

A mixture of magnesium ethoxide (22.9 g, 0.2 moles) 2,4-pentanedione (20.0 g, 0.2 moles), and ether (150 ml) was heated at reflux for 1 hour. 2,4-Dichlorobenzoyl chloride (41.9 g, 0.2 mole) in ether (50 ml) was added to the mixture over a period of 15 minutes, and the resultant mixture was heated at reflux for an additional 0.5 hour. After cooling, the reaction mixture was poured into 200 ml of 10% sulfuric acid. The ether layer was separated and stirred with 250 ml of 5% copper (II) acetate. The resulting copper salt was filtered, washed with ether, and stirred with 6N hydrochloric acid to destroy the salt. The acidic aqueous solution was extracted with ether. The ether extract was washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under vacuum yielding 21 g of the desired product as a yellow oil. It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectroscopy.

Provenance & Evidence