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Topic: Chemical Synthesis of an unknown starting with 3-(2-hydroxyphenyl)propanoic aci  (Read 2141 times)

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Offline SethFlanders

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Hello,

I am currently working on an unknown synthesis but am having some trouble.

The reaction I have found starts with 3-(2-hydroxyphenyl)propanoic acid and then Ph3P, DEAD, and THF are used in the reaction.  I have found information on the Mitsunobu Reaction that seems to use these reagents and the alcohol should be removed to and replaced with N3.  I am unable to find a product with that arrangement though.  I was wondering if anyone knew what I am doing wrong and how to figure out what the final product is.

Thanks,
Seth

Offline discodermolide

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That's all well and good but have you given us all the info.? I would thing that the Mitsunobu reaction would not work well with a free carboxylic acid present, it should maybe be an ester?
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Offline SethFlanders

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The Mitsunobu reaction was what I found that used the reagents that my synthesis showed.  I guess it is possible that it isn't a Mitsunobu reaction.  Is there another reaction using THF,DEAD, and Ph3P?

Offline discodermolide

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This reaction is used for the inversion of chiral OH centers or macrolactonisation.
To replace your OH with azide you will need a source of azide, which you don't have in your description.
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Offline SethFlanders

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The azide I have realized is not in it.  Something happens to one or both of the alcohols in the reaction.  This is a new reaction to me and I am unfamiliar with macrolactonisation.  Do both OH's invert or does only one?

Offline SethFlanders

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I also forgot that I have seen the unknown.  I am aware that it is a clear liquid at room temperature.  The odor is also odd and very strong but I have no idea how to describe it.

Also, do you know the name of the reaction in this case?  Then I can look it up and figure it out.
« Last Edit: March 15, 2013, 01:44:47 AM by SethFlanders »

Offline discodermolide

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The azide I have realized is not in it.  Something happens to one or both of the alcohols in the reaction.  This is a new reaction to me and I am unfamiliar with macrolactonisation.  Do both OH's invert or does only one?


In this molecule there are no chiral centers. You have a phenol and a carboxylic acid. Macrolactonisation is an esterification reaction, usually used to form large rings structures. What may happen here is just that and you get initially this structure.
O=C1OC2=CC=CC=C2CC1



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Offline SethFlanders

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Thank you for your help.  I have been extremely busy lately.

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