Sulfamic Acid → 9-Phenanthrenecarboxylic acid

Participants

Reaction Steps

A solution composed of the aminocinnamic acid (3 mmol), NaOH (33 mmol) and NaNO2 in water (10 mL) was added dropwise over 30 min with stirring to 48% fluoroboric acid (43 mmol) at 0-5° C. The mixture was stirred for 1 h, after which sulfamic acid was added until the mixture tested negative to starch-iodide paper. The crude solid was collected by filtration, dissolved in anhydrous acetone (10 mL) and then added dropwise with stirring over a 15 min period to ferrocene (0.056 g, 0.3 mmol) in acetone at rt. After an additional 15 min of stirring, the green reaction mixture was added to water (100 mL). A light-yellow precipitate was collected and the trace amount of ferrocene was removed in vacuo to afford the phenanthrene-9-carboxylic acid.

Provenance & Evidence