Phenanthrene-9-carboxaldehyde (Sigma Aldrich, 97%)
Acetone (Sigma Aldrich, 99%)
Sodium Hydroxide (NaOH)
Methanol 

A solution of acetone (0.0171 g, 0.29 mmol, 1.0 eq) in methanol (1 mL) at room temperature was added to a stirred solution of phenanthrene-9-carboxaldehyde (0.154 g, 0.75 mmol, 2.5 eq) in methanol (45 mL). NaOH (0.9996 g, 25.00 mmol, 84.8 eq) was dissolved into the reaction mixture. The reaction mixture was stirred at room temperature for 72 hours. The precipitated product was recovered by suction filtration, washed 1x with 2-3mL of water and washed 1x with 2-3mL of methanol, and dried over suction. The crude product was recrystallized in benzene, cooled to room temperature, washed 1x with 2-3mL of benzene, dried over suction, and recovered (0.0242 g, 19%) as yellow crystals (mp 264-265°C).  

¹H NMR Spectrum (500 MHz, CDCl₃): δ 8.78 (d, 2H), δ 8.72 (d, 2H), δ 8.68 (d, J = 16.5 Hz, 2H), δ 8.33 (d, 2H), δ 8.16 (s, 2H), δ 7.98 (d, 2H), δ 7.69 (m, 8H), δ 7.36 (d, J = 15.5 Hz, 2H) 

M. J. McBride, J. C. Bradley. UsefulChem, Experiment 286. http://usefulchem.wikispaces.com/EXP286