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Topic: 26th problem IChO - A heterocyclic compound  (Read 4885 times)

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Offline Radu

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26th problem IChO - A heterocyclic compound
« on: February 10, 2014, 06:02:43 PM »
http://icho2014.hus.edu.vn/document/01-24-2014%20IChO46-Preparatory.pdf

      My question is regarding 26.3 . I have to obtain compound C starting from levulic acid. You have my work attached, I simply cannot figure out the role of m-NO2-C6H4-SO3Na in this synthesis.

Offline Leroi

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Re: 26th problem IChO - A heterocyclic compound
« Reply #1 on: April 01, 2014, 03:06:53 PM »
i used it as base, even though it's a poor one... Please tell me whether the use of piperidine as condensation catalyst asks for caution because of the carboxylic group or you may simply mix PhCHO, levulic acid and piperidine in a flask, waiting for the reaction to take place

Offline Radu

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Re: 26th problem IChO - A heterocyclic compound
« Reply #2 on: April 02, 2014, 07:30:58 AM »
 Humm, I really don't think that amidic nitrogen can be alkylated, especially with such a weak base. If I am to use it as a weak base, I'd use it with hydrazine, to react with that acid chloride. ( a weak base is required, we have a carbonyl group that must be protected).

Offline Guvanch

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Re: 26th problem IChO - A heterocyclic compound
« Reply #3 on: April 06, 2014, 07:54:12 AM »
will you participate 46th icho.

Offline momoho

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Re: 26th problem IChO - A heterocyclic compound
« Reply #4 on: April 07, 2014, 01:49:05 PM »
http://icho2014.hus.edu.vn/document/01-24-2014%20IChO46-Preparatory.pdf

      My question is regarding 26.3 . I have to obtain compound C starting from levulic acid. You have my work attached, I simply cannot figure out the role of m-NO2-C6H4-SO3Na in this synthesis.
Hi
I am beginner in chemistry...so i will glad to see your answer to question number 25 (cefalotin) if U solve it?
Can i have your answer to this problem?

Offline Rutherford

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Re: 26th problem IChO - A heterocyclic compound
« Reply #5 on: April 22, 2014, 03:46:15 PM »
Did anyone figure out the role of m-NO2-C6H4-SO3Na?

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