1. Set up an immersion heater in a 400 mL beaker with 300 mL of water
2. Break up a cinnamon stick into small slivers (15 x 3 mm). Place the pieces into a tarred reaction vial and mass
the cinnamon and vial. Use about 1.5-2.0 g of cinnamon. Record the mass of the vial and vial/cinnamon
3. Add 5 mL of tap water to the reaction vial and seal the flask with a Teflon-coated cap.
4. Place the vial into the hot water and check for bubbles. If bubbles appear, remove the vial and tighten the cap.
5. Heat the vial for 25 minutes. After 25 minutes, remove the vial and allow to air cool for a few minutes. After
cool, place into a beaker with cold water for about three minutes.
6. Open the vial slowly. Remove the aqueous solution of cinnamaldehyde into a clean reaction vial. Do not transfer
any of the cinnamon pieces. These may be discarded into the garbage.
7. Smell the mixture. Record.
STOP FOR THE DAY. CLEAN UP YOUR LAB. LABEL YOUR VIAL CLEARLY AND SET ASIDE FOR
TOMORROW.
8. Extract the cinnamaldehyde with ethyl ether. Add about 2-3 mL of ethyl ether to the aqueous solution. Tightly
cap the vial and mix the two layers by inverting the vial several times. Be careful not to shake the vial as an
emulsion (layer of bubbles between the two layers) can be created thus increasing the separation time.
9. Allow the two layers to separate. Transfer the upper organic solvent layer into a clean reaction vial using a
pipette. This layer will contain ethyl ether and cinnamaldehyde.
10. Repeat steps 10 and 11. Combine the ethyl ether solutions from the two extractions into one reaction vial.
11. Dry the cinnamaldehyde solution with anhydrous magnesium sulfate. Add only a small amount (~2-3 mm on
the bottom of the vial). If the magnesium sulfate is clumped up, add a little more until the magnesium sulfate stops
clumping. Transfer the ethyl ether solution containing cinnamaldehyde to a clean, tarred evaporating dish using a
pipette. Rinse the magnesium sulfate with 2-3 mL of clean ethyl ether and combine with the cinnamaldehyde
solution in the evaporating dish. Record the mass of evaporating dish and evaporating dish /cinnamaldehyde
solution.
12. Place the evaporating dish in a fume hood for 5-10 minutes allowing the ethyl ether to evaporate. Small
droplets of cinnamaldehyde will remain after all the ethyl ether has evaporated. Ethyl ether has a low boiling point
(40-70 oC). Cinnamaldehyde has a boiling point of 248 oC.
13. Smell the evaporating dish after all the ethyl ether has evaporated. The oily droplets will have a strong
cinnamon smell.
2. Break up a cinnamon stick into small slivers (15 x 3 mm). Place the pieces into a tarred reaction vial and mass
the cinnamon and vial. Use about 1.5-2.0 g of cinnamon. Record the mass of the vial and vial/cinnamon
3. Add 5 mL of tap water to the reaction vial and seal the flask with a Teflon-coated cap.
4. Place the vial into the hot water and check for bubbles. If bubbles appear, remove the vial and tighten the cap.
5. Heat the vial for 25 minutes. After 25 minutes, remove the vial and allow to air cool for a few minutes. After
cool, place into a beaker with cold water for about three minutes.
6. Open the vial slowly. Remove the aqueous solution of cinnamaldehyde into a clean reaction vial. Do not transfer
any of the cinnamon pieces. These may be discarded into the garbage.
7. Smell the mixture. Record.
STOP FOR THE DAY. CLEAN UP YOUR LAB. LABEL YOUR VIAL CLEARLY AND SET ASIDE FOR
TOMORROW.
8. Extract the cinnamaldehyde with ethyl ether. Add about 2-3 mL of ethyl ether to the aqueous solution. Tightly
cap the vial and mix the two layers by inverting the vial several times. Be careful not to shake the vial as an
emulsion (layer of bubbles between the two layers) can be created thus increasing the separation time.
9. Allow the two layers to separate. Transfer the upper organic solvent layer into a clean reaction vial using a
pipette. This layer will contain ethyl ether and cinnamaldehyde.
10. Repeat steps 10 and 11. Combine the ethyl ether solutions from the two extractions into one reaction vial.
11. Dry the cinnamaldehyde solution with anhydrous magnesium sulfate. Add only a small amount (~2-3 mm on
the bottom of the vial). If the magnesium sulfate is clumped up, add a little more until the magnesium sulfate stops
clumping. Transfer the ethyl ether solution containing cinnamaldehyde to a clean, tarred evaporating dish using a
pipette. Rinse the magnesium sulfate with 2-3 mL of clean ethyl ether and combine with the cinnamaldehyde
solution in the evaporating dish. Record the mass of evaporating dish and evaporating dish /cinnamaldehyde
solution.
12. Place the evaporating dish in a fume hood for 5-10 minutes allowing the ethyl ether to evaporate. Small
droplets of cinnamaldehyde will remain after all the ethyl ether has evaporated. Ethyl ether has a low boiling point
(40-70 oC). Cinnamaldehyde has a boiling point of 248 oC.
13. Smell the evaporating dish after all the ethyl ether has evaporated. The oily droplets will have a strong
cinnamon smell.