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Topic: Synthesis of the 4-methylformyl benzoate  (Read 1015 times)

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Offline Alcane2214

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Synthesis of the 4-methylformyl benzoate
« on: June 28, 2019, 04:33:38 PM »
Hi everyone

I have a challenge exercice to do to get my organic chemistry better. I need to synthetize the 4-methylformyl benzoate from the 4-methyl benzaldehyde.

After major search, i found a way to do my molecule, but i didn't find some info i will definitely need on this synthesis. My starting material is the 4-methyl benzaldehyde, and i want to protect the aldehyde founction, so i found the ethylene glycol protection group. But will it protect it from KMnO4?? If not, anybody can hint me about a reagent or something that could help me?

My reaction patern is this:
1-protect aldehyde with ethylene glycol
2-Oxydize the CH3 by KMnO4 to make an acid
3-Unprotect my aldehyde function
4-reduce my acid to ester function by Fischer esterification.

It it a possible way or do i miss something?

Thank you :)

Offline OrganicDan96

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Re: Synthesis of the 4-methylformyl benzoate
« Reply #1 on: June 28, 2019, 05:45:44 PM »

4-reduce my acid to ester function by Fischer esterification.


that's not a reduction.

i don't think your scheme is the best way of making this compound. its probably best to make the aldehyde last as it's the most reactive functionality.

i would expect your protecting group is probably ok.
 

Offline Alcane2214

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Re: Synthesis of the 4-methylformyl benzoate
« Reply #2 on: June 28, 2019, 05:57:06 PM »
Hi

Thank you for your answer :)

Sadly, the starting material is imposed :( I tough the same, like starting with toluene, make the acid by KMnO4 and then do a Friedel-Kraft to add the aldehyde.

Thank you

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