[IndyAssassin92]

Hello everybody,
This is my first post so sorry if I have done anything wrong. I have a 3-step synthesis question that was given to me on my last exam. I sat there and stared at it forever not knowing where to start. Like stated, it has three steps and two intermediates. This will become very clear with the attached PDF document. The PDF is what I remember it looking like from the exam so hopefully it's correct. To be of further assistance, the text book I am using is David Klein's Organic Chemistry. It is the white one with test tubes. The material covered for this particular exam was from chapters 21 and 22. The professor said he would only take material from these two chapters to make the 3-step question. Who knows if that is true or not. Any help would be greatly appreciated.

Brandon T. Christie

[discodermolide]

Try and simplify it by working backwards from the product.
What has been added, what has changed?

[IndyAssassin92]

I've tried a few ideas, but my biggest issue is the carboxylic acid off of the carbon chain. Obviously turning an alkane off of a benzene into a carboxylic acid is simple, but the placement of the carboxylic acid in this problem has me completely confused.

I initially thought oxidation as an initial step, but that would oxidize the methyl group off the benzene ring too, which the product doesn't have.

[orgopete]

... it has three steps and two intermediates ... the text book I am using is David Klein's Organic Chemistry ... from chapters 21 and 22. The professor said he would only take material from these two chapters to make the 3-step question.

I'm usually decent at solving these problems, but I am skeptical this can be done in three steps and two intermediates. The problem looks suspiciously like an acetoacetate problem, but drawn incorrectly.

[IndyAssassin92]

It very well could be. I was going off memory from what I saw on my exam.

[orgopete]

If you move the COOH, can you now solve it?