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Topic: Increasing self-Claisen condensation yields  (Read 5574 times)

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Offline Erythromycin

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Increasing self-Claisen condensation yields
« on: July 26, 2007, 06:08:21 AM »
I'm trying to condense phenylpropionate into the corresponding beta keto ester. My yields are 5-15%. I have tried using both LDA and sodium hydride, varying the molar ratios of each. I have also tried temperatures up to 100 C. I do the work-up with acid following the reaction. Are there any Claisen experts out there who can help me? Thank you!

Offline russellm72

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Re: Increasing self-Claisen condensation yields
« Reply #1 on: July 30, 2007, 01:21:45 PM »
Haven't done one since i was doing my undergraduate studies and it wasn't self condensation. I used NaOMe/MeOH at reflux.

Have u checked the condition of your phenyl propionate? NMR and made sure its dry. I'm guessing its an oil and if so have u distilled it fresh prior to use.


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