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Duong_Experiment5 - Richard Duong Chem 262L Joseph Sokol 25...

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Richard Duong Chem 262L Joseph Sokol 25 March 2010 Experiment V: A Wittig Reaction-Preparation of p-methoxycinnamic acid Purpose : To create solid, carboxylic acid from an initial product from subsequent hydrolysis involving formation of ylides and esters. H 3 CO H O H 3 CO COOH 1.A 2. OH, heat 3. H Procedure : Two test tubes and a 5-mL round bottom flask containing a stir bar were dried in a heat oven for 15 minutes. 2.0 mL of 1.2 M sodium methoxide was transferred into the round bottom flask and was stirred with the flask stopped in order to prevent moisture. 0.54 g (2.4 mmol) of triethylphosphonoacetate was transferred into the first test tube while 0.33 g (2.4 mmol) of p-anisaldehyde was transferred to the second test tube.
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The triethyl phosphonoacetate was added dropwise slowly to the methoxide solution until there was none left. The solution was stirred for 5 minutes and then allowed to cool in an ice bath. The solution remained clear. The p-anisaldehyde was then added to the ylide solution slowly dropwise until none was left.
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