Diethylene Glycol → 9H-fluorene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

2-Carboxyfluorenone (12.3 g, 0.05 mole) and diethylene glycol were added to a 500 mL round bottom flask. Sodium hydroxide (7.65 g, 0.19 mole) and hydrazine hydrate (9.16 mL, 0.23 mole) were added to the solution. The temperature of the reaction was increased to 125° C. Heating was continued for three hours and then the vessel was cooled to room temperature. Distilled water (1.5 L) was added. The product was precipitated with concentrated hydrochloric acid. The product was filtered and rinsed with distilled water (2 L). The solids were dissolved in 0.5 M sodium hydroxide (2.8 L) and heated to 70° C. The product was precipitated with concentrated hydrochloric acid (pH approximately 2). The product was filtered and washed with distilled water (1.5 L). The 2-carboxyfluorene was dried overnight under reduced pressure with phosphorus pentoxide present. NMR confirmed the structure by the appearance of two new protons at δ4.01 ppm.

Provenance & Evidence