Hydroxide → 9-(1,2,4-Tri-phenylimidazolyl)-2,2-dimethylnonanoic acid

Participants

Reaction Steps

A mixture of 2,4,5-triphenylimidazole (4.13 g), ethyl 9-bromo-2,2-dimethylnonanoate (10.95 g), potassium carbonate (10 g) and 2-butanone was stirred at reflux for 48 hours. The mixture was filtered, solvent removed under reduced pressure and the residue was chromatographed on silica gel eluted with chloroform to give a clear oil which was dissolved in dimethyl sulphoxide (30 ml) and treated with potassinm 5 hydroxide (3 g). The mixture was stirred at 40° C. for 24 hours when the solvent was removed under reduced pressure. Water (50 ml ) was added, the pH of the solution was adjusted to 4 and the aqueous was extracted with chloroform (3×50 ml ). The chloroform extracts were dried over magnesium sulphate, filtered and the solvent removed to give a solid which was recrystallised from acetonitrile to give 9-(1,2,4-tri-phenylimidazolyl)-2,2-dimethylnonanoic acid as a white crystalline solid, m.p. 119°-120° C.; Found: C, 79.85; H, 7.64; N, 6.23% (C32H36N2O2); Requires: C, 79.96; H, 5.54; N, 5.82%

Provenance & Evidence