Robert Runfola

Preparation of 1,4-diphenyl-1,3-butadiene
- measure 0.38 g of benzyltriphenylphosphonium chloride in 5mL conical vial
- record weight quickly and close bottle to avoid contact with air
- add 3 drops of pure cinnamaldehyde, then weigh again
- if less than 120mg of aldehyde add a drop and weigh again
- Add 1 mL of methylene chloride and magnetic stir vane to vial, cap vial and stir
- add 0.5mL of NaOH to vial and stir for 20 minutes
- pour vial into 6 inch test tube then rinse vial with 1 mL methylene chloride and then 3 mL of
water
- add the washings to the test tube and mix by using the Pasteur pipet and drawing up then
releasing the contents.
- let test tube stand then transfer the lower layer into another 6 inch test tube
- extract remaining aqueous layer in the first tube with 2mL portions of CH2Cl2
-dry the washings of second test tube with anhydrous magnesium sulfate and swirl for 5-10
minutes
- filter through pipet filter into third 6 inch test tare tube
- evaporate CH2Cl2 into hood using sand bath, place tube in warm sand bath
- weigh tube after liquid is gone, from tare weight calculate as crude yield
- in the hood dissolve solid in about 4 mL of boiling 95% ethanol
- allow solution to cool for 5-10 min then place tube in ice bath to complete recrystallization
- isolate crystals by centrifugation, then record weight and melting point of purified product
- calculate percent yield of recrystallized product and submit a dry sample into melting point
capillary


Name Structure MW
g/mol
MP Density g/
cm^3
Hazards
benzyltriphenylphosphonium
chloride




388.87 300 C 1.00
cinnamaldehyde


132.16 -7.5 C 1.05
methylene chloride




84.93 -96.7 C
1.33
Sodium Hydroxide



39.997 318 C 2.13