Sodium Chloride → 1,4-Bis(3-nitrophenyl)butane-1,4-dione

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Reaction Steps

Anhydrous zinc(II) chloride (5.42 g, 39.7 mmol) was stirred in dry benzene (50 mL) under nitrogen while diethylamine (3.10 mL, 29.8 mmol) and t-butanol (2.85 mL, 29.8 mmol) were added. The resulting mixture was stirred at room temperature for 90 min to give a cloudy solution. To this was added 1-(3-nitrophenyl)ethanone (4.97 g, 29.8 mmol) followed by 2-bromo-1-(3-nitrophenyl)ethanone (5.00 g, 19.87 mmol) and the resulting mixture allowed to stir at room temperature overnight. A large portion of the benzene was subsequently removed by decantation. The resulting mixture was then treated with 5% sulfuric acid (25 mL) in a separatory funnel and the aqueous phase drawn off. The organic phase was washed with water (2×25 mL). A third washing resulted in an emulsion. The contents of the funnel were emptied into a large volume of water (750 mL) to which was added sodium chloride and the oil in water mixture rapidly stirred. Methanol was added (75 mL) in portions to try and disperse the oil and promote solidification of the product. After nearly forty eight hours of stirring the product solidified and was collected by vacuum filtration. The filter cake was water washed, dried first in air and then a vacuum oven at 55° C. to provide the title compound (5.85 g, 90% yield) as a pale yellow solid that was used directly in the next step.

Provenance & Evidence