can anybody tell me how to synthesize the one on the right from the one on the left?

Question

anonymous · Answer

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jfraser · Answer

i don't remember much from organic mechanisms, but I believe you could reflux the reactant with ethanol and replace the methyl group with the ethanoate ion.

aaronq · Answer

^you need to change the methyl group to a good leaving group first. 

KMnO4 will oxidize alkanes to carboxylic acids at benzylic positions (im not sure if having a ketone present will affect this, in which case you would want to reduce it with $H_2/Pd*C$ before the oxidation)

Once you have benzoic acid you can do the reflux with an ethanol in dilute acid

aaronq · Answer

Or you can do the haloform reaction which gets rid of the methyl and leaves an OH in it's place.

jfraser · Answer

@aaronq thanks. I was thinking of the synthesis of methyl salicylate from salicylic acid, but  that already has the carboxylic leaving group

anonymous · Answer

I'm still a bit confused by this.. I'll try to review my notes and see if I can draw the mechanism. Thanks everyone!

Ochem is hard, there's so much that you have to remember...