Triethylamine → Pyrene

Participants

Reaction Steps

3,6-dioxaoctanedioic acid (0.28 mmol) was dispersed in 100 ml of dichloromethane (CH2Cl2) in which 0.1 ml of oxalyl chloride ((COCl)2) and 15 μl of DMF were added, to prepare a solution. After the solution was stirred at ambient temperature for 4 hours, volatiles were removed from the solution and the residue was re-dissolved in a small amount of dichloromethane. After the solution was added slowly to dichloromethane solution in which 152 mg (0.70 mmol) of 1-aminopyrene and 0.2 ml (1.4 mmol) of triethylamine were dissolved, the solution was reacted at ambient temperature for 4 hours and the volatiles were removed. And then, the resulting product was partitioned between water and dichloromethane and the organic phase was separated and washed with water; the solvent was removed from the obtained organic phase; and then, re-crystallization was carried out with a solvent combination of dichloromethane and methanol. The target product, a pyrene compound of 3,6-dioctanedioic acid was obtained (reddish green solid, yield: 65%).

Provenance & Evidence