Sodium Hydroxide → HCID 85692231, compound

Participants

Reaction Conditions

Reaction Steps

The Huang-Minlon method was used essentially as described in Clar and Zanders (1958), with modifications to increase the overall yield of the acid: 3-coronenoyl propionic acid (100mg), 80% hydrated hydrazine (74.8 μl), NaOH (60mg), and diethylene glycol (249μl) were combined in a 5ml round-bottomed flask. The mixture was refluxed for 90 minutes at 180° C, then water and excess hydrazine hydrate were distilled off until the temperature rose to 200° C. The mixture was refluxed for an additional 3.5 hours at 195° C., cooled to room temperature and diluted with water and 2M HCl. The resulting solid was collected by vacuum filtration and washed with cold water and 2M HCl. The product was recrystallized from xylene, dried under vacuum for 48 hours. 50mg of crystalline product was further purified by flash chromatography on a silica gel G column (100cm×2.5cm; 40 micron particle size) with a nitrogen pressure of 5-10 p.s.i. using ethyl acetate/xylene (2:1; v/v) as the running solvent. The eluant was tested using TLC (silica gel G plates) and THF/xylene (1:1; v/v) as the running solvent. The pure 4-coronenyl butyric acid (FIG. 1, compound III) exhibited a single spot (Rf=0.65) under these conditions. Fractions containing pure product were pooled and dried by rotary evaporation. A yield of 86% was obtained (66.4 mg) with a melting point of 273° C. IR and NMR analysis showed spectra consistent with the expected product. Compound III in THF had an absorption band ε294 =23,644±97 80M-1 cm-1.

Provenance & Evidence