Aldol condensation of phenanthrene-9-carboxaldehyde and acetone; (1E,4E)-1,5-Di(9-phenanthryl)-1,4-pentadien-3-one
SyntheticPage 774
DOI:
10.1039/SP774
Submitted Jan 28, 2015, published Jan 29, 2015
Matthew McBride (
mcbridemj@gmail.com), Jean-Claude Bradley (
)
A contribution from
UsefulChem
Chemicals Used
Phenanthrene-9-carboxaldehyde (Sigma Aldrich, 97%)
Acetone (Sigma Aldrich, 99%)
Sodium Hydroxide (NaOH)
Methanol
Procedure
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).
Author's Comments
•The product was insoluble in methanol allowing for recovery by filtration.
•A trace impurity of benzene was present in the final product as determined by the NMR spectrum.
Data
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)
Lead Reference
M. J. McBride, J. C. Bradley. UsefulChem, Experiment 286.
http://usefulchem.wikispaces.com/EXP286
Supplementary Information
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Keywords: Aldol Condensation