Synthesis of Isoborneol
by Markus Arnoldini
Laboratory Report
Synthesis of
Isoborneol
OH
H
by Markus Arnoldini
1
Synthesis of Isoborneol
1.
by Markus Arnoldini
Method
Reduction of camphor to isoborneol with NaBH4.
2.
Reaction Equation
NaBH4
OH
O
3.
H
Mechanism
+
4
H
H
Na
B
H
4
O
H
O
H
4 H2O
+
4
OH
H
2
NaB(OH)4
Synthesis of Isoborneol
4.
by Markus Arnoldini
Physical properties of the substances
Camphor [1]
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
O
S-phrases
152.24 g/mol
0.99 g/cm3 (20 ºC)
175 - 180 ºC
~ 210 ºC
1
3
R 11 (Highly flammable)
R 36/37/38 (Irritating to
eyes, respiratory system
and skin)
-
Ethanol [1]
molar weight
density
H2
C
H3C
OH
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
46.07 g/mol
0.790 - 0.793 g/cm3
(20 ºC)
-114.5 ºC
78.3 ºC
1
R 11 (Highly flammable)
S 7 (Keep container tightly
closed)
S 16 (Keep away from
sources of ignition - No
smoking)
Magnesium sulfate [1]
MgSO4
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
3
120.37 g/mol
2.66 g/cm3 (20 ºC)
1
-
Synthesis of Isoborneol
by Markus Arnoldini
Sodium tetrahydridoborate [1]
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
NaBH4
37.83 g/mol
1.07 g/cm3 (20 ºC)
~ 400 ºC (langsame
Zersetzung)
~ 500 ºC
2
3
R 15 (Contact with water
liberates extremely
flammable gases)
R 25 (Toxic if swallowed)
R 34 (Causes burns)
S 14.2 (Keep away from
oxidizing and acidic agents
and heavy metal
compounds)
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 43.6 (In case of fire use
sand. Never use water)
S 45 (In case of accident
or if you feel unwell, seek
medical advice
immediately. Show the
label where possible)
Isoborneol [1]
OH
H
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
4
154.25 g/mol
205 - 208 ºC
210 ºC
2
-
Synthesis of Isoborneol
by Markus Arnoldini
Diethylether (anhydrous) [1]
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
O
S-phrases
5.
74.12 g/mol
0.71 g/cm3
-116.3 ºC
34.6 ºC (1013 hPa)
1
4
R 12 (Extremely
flammable)
R 19 (May form explosive
peroxides)
R 22 (Harmful if
swallowed)
R 66 (Repeated exposure
may cause skin dryness or
cracking)
R 67 (Vapours may cause
drowsiness and dizziness)
S 9 (Keep container in a
well-ventilated place)
S 16 (Keep away from
sources of ignition - No
smoking)
S 29 (Do not empty into
drains)
S 33 (Take precautionary
measures against static
discharges)
Experimental accomplishment
In a 50 mL round-bottom flask 0.5 g (0.003 mol) of champhor and 20 mL of waterfree
EtOH were put. Once the solid was completely dissolved, 0.6 g of NaBH4 were added
slowly with a spatula. The flask did not get hot, but an ice bath was prepared for the
case. After the addition the solution was brought to the boiling point and kept there
for 2 min. At this point the solution was poured onto 15 g of crushed ice. After the ice
had melted, more water was added until white clouds of solid were visible. Then the
EtOH was removed in the rotovap. The solid was then filtered off, dissovled in 20 mL
of Et2O and dried with MgSO4. The solvent was then removed with a rotovap. An
amount of 0.27 g (0.0017 mol) of product 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 56.6 %:
0.0017 mol
 100%  56.6%
0.003mol
5
Synthesis of Isoborneol
6.
by Markus Arnoldini
Experimental setup
LaboBib©
300
50
1500
AN
AN
AUS
AUS 1000
0 U/min
250
100
500
o
C
200
7.
150
750
Analytical results
Melting point:
170-203 °C
Peaks in IR Spectrum (in cm-1):
3200-3500:
2050-3000:
1700-1770:
O-H
C-H
C=O (probably from reactand)
8.
Sources
[1]
[2]
http://ch.chemdat.info/mda/ch/de/
meanings of R-phrases:
http://www.chemie.fu-berlin.de/chemistry/safety/r-saetze_en.html
meanings of S-phrases:
http://www.chemie.fu-berlin.de/chemistry/safety/s-saetze_en.html
[3]
6
Synthesis of Isoborneol
by Markus Arnoldini
7