262-5 - Anusha Vadlamudi TA: Lindsay Aldridge Chem 262 L...

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Anusha Vadlamudi TA: Lindsay Aldridge Chem 262 L 401; Rm: 300 Experiment 5: A Wittig Reaction: Preparation of a para-methoxycinnamic acid A 5-mL round bottomed flask and two test tubes were dried in a drying oven for 10 minutes but were not cooled to room temperature in a desiccator. To a flask, 2 mL 1.2 N NaOCH 3 was added using a disposable pipette instead of a burette. To the flask, 0.538 g (2.4 mmol) triethylphosphonoacetate was added slowly, using a disposable pipette. The solution was stirred for 5 minutes then cooled in an ice bath for about 5 minutes. Into a test tube, 0.328 g (2.4 mmol) p-anisaldehyde was measured and then slowly added to the ylide solution using a pipette. The solution was warmed to room temperature then stirred for 15 minutes. To this, 3 mL of 5% NaOH were added. The solution was then transferred to a Erlenmeyer flask and heated directly on the hot plate on low heat for 30 minutes. To the flask, H 2 SO 4 was added dropwise until a pH of 2 was reached. The crude product was filtered then recrystallized from ethanol-water. A minimal amount of
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This note was uploaded on 02/23/2010 for the course CHEM 262L taught by Professor Mbadugua during the Spring '08 term at UNC.

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262-5 - Anusha Vadlamudi TA: Lindsay Aldridge Chem 262 L...

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