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Chemiluminescence Ester Formation - Divanillyl Oxalate

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oesan1:
The question is

Provide a mechanism for the first nucleophilic attack of vanillin on oxalyl chloride and stop at the formation of the first ester.


But where do you attack first? Is it alcohol on chloride first? How do you begin?

Babcock_Hall:
Why don't you draw and post what you think is correct?

oesan1:
Of course! I tried attacking from the ketone instead of the alcohol. 8)

rolnor:
Here is the structure of vanillin, its an aldehyde, not a ketone. You have a hydroxy group on vanilline, maybe it is important?


https://sv.wikipedia.org/wiki/Vanillin

oesan1:
Yeah, I realized that, forgot to add the hydrogen. Wouldn't the only difference be a balanced oxygen group (the one near the ester)?

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