4-Formylbenzoic acid → 4-[6-(2-Imidazole-1-yl-ethoxy)-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidenemethyl]-benzoic acid

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Reaction Steps

6-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.400 g, 1.56 mmol) was reacted with 4-formyl benzoic acid (0.351 g, 2.34 mmol) in 5.0 mL of 4% KOH in EtOH and 1 mL of dioxane at room temperature for 6 days. The reaction was diluted with minimal water to achieve complete solution and then extracted with DCM. The resulting aqueous solution was acidified to pH 2 with 1N HCl. After standing at room temperature for 3 weeks, 0.061 g (10%) of the title compound was isolated by filtration as a fine cream powder, mp 267-267.5° C.: CI-MS m/e 388 (M+), 389 (M++1);

Provenance & Evidence