Organic chemistry practical course (OCP1)
WS 04/05
529-0229-00
Assistant: Fabio Di Lena
Synthesis of
9,10-dihydroanthracene-9,10-α,β-succinic
acid anhydride
O
O
O
Presented by
Moreno Wichert
Student of Interdisciplinary Natural Sciences (Biochem.-Phys.)
D-CHAB, ETH Zurich
Nuolen SZ
December 20, 2004
1. Method
Maleic anhydride undergoes a Diels-Alder [4+2]-cycloaddtion with anthracene.
2. Chemical equation
O
O
O
O
o-xylene
solvent
∆ 160 °C
O
O
C14H10
C4H2O3
C18H12O3
178.23 g mol-1
98.06 g mol-1
276.29 g mol-1
3. Mechanism
O
O
O
O
o-xylene
solvent
∆ 160 °C
O
O
4. Experimental accomplishment
3.2 g of anthracene1 and 1.7 g maleic acid2 were dissolved in o-xylene3 in a round-bottom
flask. The solution was refluxed for two hours and then cooled down in the fridge to form
crystals. The reaction product (9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride4)
was filtered through a sintered glass funnel.
Physical and safety data of the substances
1)
C14H10 ; M = 178.23 g mol-1 ; ρ = 1.24 g cm-3 ; melting point = 216 - 218 °C ;
boiling point = 340 °C ; poison class 4 ; WGK 2 ; risk phrases: R 36-37-38-42-43 ;
safety phrases: S2-26-36-37-39
2)
C4H2O3 ; M = 98.06 g mol-1 ; ρ = 1.32 g cm-3 ; melting point = 52 °C ; boiling point = 200 °C ;
poison class 3 ; WGK 1 ; risk phrases: R22-34-42-43 ; safety phrases: S22-26-36-37-39-45 ;
MAK: 0.4 mg m3
3)
C8H10 ; M = 106.17 g mol-1 ; ρ = 0.88 g cm-3 ; melting point = -25 °C ; boiling point = 144 °C ;
poison class 4 ; WGK 2 ; risk phrases: R11-20-21-38 ; safety phrases: S25
4)
C18H12O3 ; M = 276.29 g mol-1 ; no other data available
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Refluxing apparatus with Dimroth condenser
a sintered glass funnel
5. Analytical results and characterization
Yield after filtration: 3.2 g (58 %)
Measured melting point: 262 - 265 °C
IR bands [cm-1]:
3018 (C-H stretch)
1786 (anhydric group)
1223-1209 (anhydric group)
793-770 (neighbouring aromatic C-H)
6. Literature
Bülle, Jan; Hüttermann, Aloys (2000): Das Basiswissen der organischen Chemie, Stuttgart
(Georg Thieme Verlag)
Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. (1994): Organische Chemie (2. Auflage),
Weinheim (VCH Verlagsgesellschaft mbH)
http://www.physicspost.com/science-article-74.html
http://members.tripod.com/~EppE/dielsald.htm
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