Sulfuric Acid → HCID 13603942, compound

Participants

Reaction Steps

To a solution of 350 g of concentrated sulfuric acid and 350 ml of water cooled to 0° C., 40 g of ethyl 4-(4-aminophenyl)pentanoate was added dropwise, maintaining the temperature at 0°-2° C. The mixture was then treated dropwise with 13.66 g of sodium nitrite in 25 ml of water at such a rate that the temperature did not exceed 2° C. The resultant solution was added dropwise to a refluxing solution of 387 g of copper sulfate in 600 ml of water over a period of approximately 30 minutes. The mixture was refluxed an additional 10 minutes, cooled to room temperature, and 800 ml of water was added. The mixture was extracted thrice with dichloromethane (additional water was needed to dissolve the salts). The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and evaporated to give an oil. The oil was distilled at 0.6 mm to give 21.05 g (53%) of product, b.p. 129° C., which crystallized on cooling, m.p. 32°-34° C.

Provenance & Evidence