Succinic anhydride → HCID 54489600, compound

Participants

Reaction Steps

A Friedel-Crafts acylation of coronene was performed using the procedure of Clar and Zanders J. Chem. Soc. 2, (1958) 1577-1579, with the Coronene (100mg; FIG. 1, compound I) and succinic anhydride (73.4mg) were placed in a 10ml round-bottomed flask. Aluminum chloride (400mg) was dissolved in 3ml of nitrobenzene and injected slowly into the round-bottomed flask. The flask was then flushed with nitrogen and sealed. The mixture was stirred for four hours and cold 2M HCl (8ml) was added and the solution boiled for 10 minutes. A greenish-yellow precipitate was obtained. The crystals were filtered, washed with benzene, methanol and 2M HCl, and dried overnight under vacuum. The product (108mg; 82% yield) was recrystallized from xylene and judged pure using TLC analyses (Rf=0.53), using 50% ethanol/50% THF (v/v) as the developing solvent with silica gel G (40 micron) as the support medium. The keto-acid (FIG. 1, compound II) had a melting point of 243° C. IR and NMR analysis gave spectra consistent with the structure of the molecule, and in xylene had an absorption band at 444 nm, with ε340 in THF=24,914±80M-1 cm-1.

Provenance & Evidence