Topic: Is this a Claisen Condensation? (Read 1904 times)

mglbs · « **on:** July 16, 2021, 09:06:16 AM »

Can someone please check if I did this right?
https://photos.google.com/share/AF1QipN_oys9z5nj5Qga3GyL0nZxRx_XNSuQIF7FMk85ReljDmq96sQ8lBEhDZeJk8gE2g?key=RUdHRmR2RjdBc1pKcWRDX2NxSHhydXc3MnZ5dkZn

Babcock_Hall · « **Reply #1 on:** July 16, 2021, 12:11:21 PM »

Is it possible that the acid will catalyze a further reaction?
EDT
Are you sure that your benzyl group is in the correct place from a regiochemistry perspective? Might be worth drawing curved arrows.

Meter · « **Reply #2 on:** July 16, 2021, 01:47:10 PM »

It is not quite a Claisen condensation, as this is a reaction between two esters (crossed Claisen condensations occur between an ester and some other carbonyl, like a ketone).

rolnor · « **Reply #3 on:** July 17, 2021, 01:47:06 AM »

https://en.wikipedia.org/wiki/Malonic_ester_synthesis

Meter · « **Reply #4 on:** July 17, 2021, 07:32:41 AM »

Quote from: rolnor on July 17, 2021, 01:47:06 AM

https://en.wikipedia.org/wiki/Malonic_ester_synthesis

Oh, I never really looked at the Malonic ester synthesis that way.

It's essentially a way of making a custom ester. Would you use transesterification to change the O-R moiety?

Babcock_Hall · « **Reply #5 on:** July 17, 2021, 03:55:10 PM »

@OP, After the removal of the proton, which atom is the nucleophile with respect to the benzylic carbon?

rolnor · « **Reply #6 on:** July 18, 2021, 04:14:38 PM »

OK, now I saw the link in the top Babcock, yes, it is the wrong carbon acting as nucleophile.

Topic: Is this a Claisen Condensation? (Read 1904 times)

mglbs

Is this a Claisen Condensation?

Babcock_Hall

Re: Is this a Claisen Condensation?

Meter

Re: Is this a Claisen Condensation?

rolnor

Re: Is this a Claisen Condensation?

Meter

Re: Is this a Claisen Condensation?

Babcock_Hall

Re: Is this a Claisen Condensation?

rolnor

Re: Is this a Claisen Condensation?

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