Experimental procedure:

1. To a 100 ml erlenmeyerflask add 5 mL of benzaldehyde and 30 mL of 10% potassium

carbonate solution. MAKE sure to stir very much. For 1 minute. Decant mixture into a
test tube and allow layers to separate.
2. While the layers separate: suspend 7.78 g of benzyltriphenylphosphonium chloride in
15 mL of dichloromethane in an erlendmeyer flask with a magnetic stirrer.
3. In a 250 mL erlendmeyer flask dissolve 50 g of sodium hydroxide in 75 mL of distilled
water. Let it cool.
4. While the sodium hydroxide is cooling: carefully remove the purified benzenaldehyde
from the aqueous potassium carbonate (the top layer). Then add 2 mL of the
benzenaldehyde to the reaction mixture. Then add the sodium hydroxide.
5. Clamp the flask, plug the neck with cotton, and stir very much for 30 minutes. Decant
mixture into a sep. funnel through a filter funnel. Rinse the reaction flask and stirrer
bar with 20x2 mL of dichloromethane and water 15 mL.
6. Separate the mixture. Dichloromethane should be at top. DO NOT discard any phases.
Dry the dichloromethane with MgSO4. Filter solution. Save some for TLC.
7. Rotvap solution. Triturate the residue many times with hot light petroleum(25 mL
portions).
8. Save some of the mix. Consentrate to 25 mL on rotvap. Add a crystal of iodine. Heat
at reflux. See fig, for 30 minutes. Allow to cool.
9. Transfer to sep Kolbe. Add 10 mL of metabisulfide solution. Remove the lower aqeous
layer and add 25 mL of methanol to the organic phase in sepkolbe. If two phases do
not form, see book. Separate upper layer of light petroleum. Dry over mgso4. Filter
and rot vap. FKN WEIGH THE FLASK.