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Topic: In need of feedback about mechanism  (Read 1275 times)

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Offline Ebbe Loos

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In need of feedback about mechanism
« on: April 28, 2022, 10:36:56 AM »
Hi,

For my project, i need to synthesise a molecule. I've come up with a mechanism which you can see in the picture.

The experimental workup, i need to follow:

A mixture of azulene (with the 2 esthers) (300mg.) and a 2N potassium
hydroxide solution (2ml.) in ethanol (8ml.) was
heated under reflux for 3hr. The reaction mixture
was then diluted with water, acidified with 6N
hydrochloric acid, and extracted with ether. The
oily material obtained by the evaporation of the
solvent was dissolved in benzene and chromato-
graphed through a silica gel column. The eva-
poration of the solvent from the effluent left
crystals, which were recrystallized from ethanol
gave XV (150mg.) as red needles

Edit: the proton of the carboxylicacid comes from the HCl added in experimental workup.

Thanks in advance!
Ebbe

Offline Ebbe Loos

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Re: In need of feedback about mechanism
« Reply #1 on: April 28, 2022, 10:57:47 AM »
I found a better mechanism involving the loss of CO2 gas and the formation of alcohol. Can someone confirm which one is correct?

Offline sjb

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Re: In need of feedback about mechanism
« Reply #2 on: April 28, 2022, 03:19:06 PM »
It may be difficult to tell - but experimentally, do you see gas evolution for instance?

Offline rolnor

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Re: In need of feedback about mechanism
« Reply #3 on: April 28, 2022, 04:47:51 PM »
You will hydrolyze the ester first?

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