THE DIELS-ALDER REACTION OF ANTHRACENE

WITH MALEIC ANHYDRIDE

February 1, 2001

Jacqueline H. Ramirez

Objective:

Use the Diels-Alder reaction to form a bridged polycyclic anhydride. Recrystallize the product and characterize it by using melting point and infrared spectroscopy.

Reagents and Properties:

Substance	Quantity	Molar mass (g/mol)	MP (^oC)	BP (^oC)
anthracene	100 mg	178.23	216-218	-
9,10 dihydroanthracene-9, 10-α,β-succinic anhydride*	-	276.29	262-264	-
Maleic anhydride	55 mg	98.06	54-56	200
Potassium bromide	100 mg	-	-	-
xylene	6 ml	106.17	-	137-144

* product

Chemical alert:

Anthracene- irritant

Maleic anhydride- toxic and corrosive

Potassium bromide-irritant and hygroscopic

Xylene- flammable and irritant

Procedure:

• Weigh anthracene and maleic acid
• Place weighed reagents in a conical vial; add xylene
• Assemble a reflux apparatus
• Heat anthracene and maleic anhydride at reflux for 30 minutes
• Cool the reaction mixture in an ice bath
• Use vacuum filtration to collect the crude product
• Weight the crude product
• Recrystallize the product from xylene
• Use vacuum filtration to collect the purified product
• Dry the purified on a watch glass
• Weight the purified product
• Measure the melting points of both purified and crude products
• Take an IR spectrum of the product.

Reaction: C₁₄H₁₀ + C₄H₂O₃ ---à C₁₈H₁₂O₃