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Wittig - Amy Linkous CHEM 2556 CRN 91653 Wittig Reaction...

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Amy Linkous 11/4/09 CHEM 2556, CRN: 91653 Wittig Reaction Objective: To synthesize E,E-1,4-diphenyl-1,3-butadiene by use of the Wittig reaction with a phosphorus ylide. General Reaction: Procedure: 0.45 g of sodium hydroxide (60% in oil) was weighed out and transferred to a round- bottom flask set up for reflux and addition with protection from atmospheric moisture. 15 mL dry diethyl ether was added and the mixture was gently stirred for one minute. The mixture was allowed to settle and the supernatant was removed by pipette. Any sodium hydroxide removed with the ether was destroyed by adding the supernatant to a beaker with 50 mL of 2-propanol.
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This process was repeated twice and a final 15 mL portion of ether was added to cover the sodium hydroxide. This was stirred gently and 2.28 g diethyl benzyl phosphate (in 10 mL diethyl ether) was added dropwise with stirring over a 5-minute period. When half of this amount had been added, addition was paused and 3 drops of dry ethanol were added to the reaction flask and the reaction was heated. When the evolution of hydrogen gas became vigorous, the heat was
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