Synthesis of 1,2,3,4-Tetraphenylnaphthalene Using a Diels-Alder Reaction

CHE 2204

Section 106

April 5th, 2016

Synthesis of 1,2,3,4-Tetraphenylnaphthalene Using a Diels-Alder Reaction

Academic Integrity Statement

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Abstract:

Using the Diels-Alder reaction, 1,2,3,4-tetraphenylnaphthalene (TPN) was synthesized under reflux from the reaction between tetraphenylcyclopentadienone (TPC) and benzyne, which was produced in situ from the reaction of anthranilic acid and isopentyl nitrite. The product was purified using rotary evaporation, trituration, and vacuum filtration. The product was then identified as 1,2,3,4-tetraphenylnaphthalene by using 13C NMR, infrared, and UV spectroscopy to compare it to the spectra of the TPC reactant..

Chemical Equation:

Formation of benzyne from anthranilic acid and isopentyl nitrite:

Formation of 1,2,3,4-tetraphenylnaphthalene from tetraphenylcyclopentadienone and benzyne:

Procedure:

For the experiment, 1.902 g of TPC (4.95 mmol) and 10.0 mL of 1,2-dimethoxyethane (96.2 mmol) were placed into a 100-mL round bottom flask (RBF). The apparatus for addition under reflux was set up and the mixture was heated until reflux began. In a small beaker, 0.803 g of anthranilic acid (5.85 mmol) was dissolved in 7.06 mL of 1,2-dimethoxyethane and placed to the side while 8.5 mL of 1.3 M isopentyl nitrite in dimethoxyethane solution was collected and placed into the separatory funnel.

Once the reaction mixture began to reflux, the anthranilic acid solution was added through the top of the condenser in a drop wise manner using a Pasteur pipette while simultaneously adding the isopentyl...