Synthesis of 9,10,11,15-tetrahydro-9,10[3’,4’]-furanoanthracen-12,14-dione
by Markus Arnoldini
Laboratory Report
Synthesis of
9,10,11,15-tetrahydro-9,10[3’,4’]furanoanthracen-12,14-dione
O
O
O
by Markus Arnoldini
1
Synthesis of 9,10,11,15-tetrahydro-9,10[3’,4’]-furanoanthracen-12,14-dione
1.
by Markus Arnoldini
Method
Diels-Alder-Reaction (4+2 cycloaddition) of anthracene with maleic acid anhydride,
using Xylene as solvent.
2.
Reaction Equation
O
O
O
O
O
+
3.
O
Mechanism
O
O
Xylene
O
2
Synthesis of 9,10,11,15-tetrahydro-9,10[3’,4’]-furanoanthracen-12,14-dione
4.
by Markus Arnoldini
Physical properties of the substances
Anthracene [1]
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
178.24 g/mol
215 - 217 ºC
2
4
-
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
98.06 g/mol
1.32 g/cm3 (55 ºC)
51 - 53 ºC
202 ºC (1013 hPa)
1
3
R 22 (harmful if
swallowed)
R 34 (causes burns)
R 42/43 (may cause
sensitisation by inhalation
and skin contact)
S-phrases
S 22 (do not breathe dust)
S 26 (in case of contact
with eyes, rinse
immediately with plenty of
water and seek medical
advice)
S 36/37/39 (wear suitable
protective clothing, gloves
and eye/face protection)
S 45 (in case of accident or
if you feel unwell, seek
medical advice
immediately, show the
label where possible)
Maleic acid anhydride [1]
O
O
O
3
Synthesis of 9,10,11,15-tetrahydro-9,10[3’,4’]-furanoanthracen-12,14-dione
by Markus Arnoldini
ortho-Xylene [1]
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
106.17 g/mol
0.88 g/cm3 (20 ºC)
-25 ºC
144.4 ºC (1013 hPa)
2
4
R 10 (flammable)
R 20/21 (harmful by
inhalation and contact with
skin)
R 38 (irritates skin)
S 25 (avoid contact with
eyes)
Calciumchloride [1]
CaCl2
5.
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
2.15 g/cm3 (20 ºC)
0.78 g/cm3 (20 ºC)
772 ºC
> 1600 ºC
1
R 36 (irritates eyes)
S 22 (do not breathe dust)
S 24 (avoid contact with
skin)
Experimental accomplishment
3.25 g (= 0.02 mol) of anthracene and 1.75 g (= 0.02 mol) of maleic acid anhydride
were put in a 500 ml round bottom flask. 100 ml of xylene were added and the
resulting mixture brought to 100 °C and stirred for about 10 min. More xylene was
added, until the entire solid was dissolved. Then the solution was refluxed for 2 h at
160 °C. It changed its color from yellow to greenish to brownish. The mixture was
then kept at room temperature over night. The next day the precipitated crystals were
filtered off, weighted and characterized. An amount of 3.90 g (= 0.014 mol) of crystal
was received.
For the calculation of the yield the molar amount of received product was
divided by the molar amount of reactants used, and then multiplied by 100. This
calculation yields a percentage of 70 %:
0.014mol
 100%  70%
0.02mol
4
Synthesis of 9,10,11,15-tetrahydro-9,10[3’,4’]-furanoanthracen-12,14-dione
6.
by Markus Arnoldini
Experimental setup
Calciumchloride duct
Reflux-cooler
Thermometer
drop-flask with xylene
three-neck round bottom flask
LaboBib©
300
50
AN
AN
1500
100
0 U/min
250
500
o
C
200
7.
150
AUS
AUS 1000
750
Analytical results
Melting point:
261.0 °C – 262.5 °C
Peaks in IR Spectrum (in cm-1):
3024:
2967:
1650-1771:
C-H (aromatic)
C-H (aliphatic)
C=O (Keto-group)
8.
Sources
[1]
[2]
http://ch.chemdat.info/mda/ch/de/
meanings of R and S phrases from Reinhard Keese: “Grundoperationen der
präparativen Organischen Chemie – Eine Einführung”, 2003, S 193-197
5
Synthesis of 9,10,11,15-tetrahydro-9,10[3’,4’]-furanoanthracen-12,14-dione
6
by Markus Arnoldini