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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Meter on June 08, 2021, 05:58:28 AM

Title: Cyclohexanecarboxylic acid from diethyl malonate?
Post by: Meter on June 08, 2021, 05:58:28 AM

Imgur is broken right now so I cannot post the reaction. But the problem asks how to synthesis cyclohexanecarboxylic acid from diethyl malonate and which reagents to use. They also want a mechanism, but that should be the least of my problems once I figure out what reagents to use.

My initial thought is to do a malonic ester synthesis with an -R group that can close under certain conditions (again, I can choose whichever reagents I want), but I still can't figure out a solution.

Any help?

Edit: Thanks, Borek.

Title: Re: Cyclohexanecarboxylic acid from diethyl malonate?
Post by: Borek on June 08, 2021, 06:22:45 AM

If the image is not too large you can easily attach it to the post here - see + Additional options... under the edit field.

Title: Re: Cyclohexanecarboxylic acid from diethyl malonate?
Post by: Meter on June 08, 2021, 07:55:04 AM

Seems like this Wikipedia article (https://en.wikipedia.org/wiki/Malonic_ester_synthesis) gives me the answer. I assume I simply have to use the C5 version of the dihalide.