Dehydration of 3,4-dihydro-5H-Benzo[cd]pyren-5-ol; 6H-Benzo[cd]pyrene
Submitted Mar 15, 2012, published May 31, 2012
Anish Mistry (email@example.com
A contribution from
Fox Group, Warwick University
Amberlyst 15 (Sigma-Aldrich)
3,4-dihydro-5H-Benzo[cd]pyren-5-ol (0.1 g, 0.39 mmol) was dissolved in chloroform (30 ml) and Aberlyst 15 (0.1 g) added under a dinitrogen atmosphere. The reaction was heated to 30oC and left overnight under the inert atmosphere. The solution was then filtered to seperate the Amberlyst and washed with chloroform. The combined solvents were removed under vacuum using a Rotary evaporator. The crude product was column chromatographed under a dinitrogen atmosphere eluting with 1:1 chloroform:petroleum ether 40-60oC. A white solid was obtained using this method (50 mg, 54%).
δH(400MHz, CDCl3) ppm: 5.00 (2H, s, -CH2), 7.46 - 7.55 (4H, m, aryl), 7.72 - 7.84 (6H, m, aryl).
1H NMR (Jan11-2012.dx)
Proton NMR shows the symmetric dihydrogen species as the major product, the small peaks which can be observed in the spectrum (around 2, 3.5 ppm and aromatic region) are presumably other isomers of the compound.1H NMR spectrum of Olympicene - Click to view
Keywords: aromatics/arenes, dehydration