[lrisNil]

Make the   following   compound from benzene. Show all   steps and   reagents.

Please be thorough, all help appreciated!

[billnotgatez]

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[OrgXemProf]

Points to consider:

1. The product bears meta substituents. Thus, you must FIRST introduce a meta-directing substituent into the benzene ring.

2. When introducing the second substitutent, the chosen electrophile must either introduce an acetyl or hydroxymethyl group directly or, alternatively, introduce a suitable functional group that can serve as a precursor to one of the two groups present in the final product.

3. Depending on the method chosen to introduce substituents into the benzene ring, it may be necessary for to perform additional reactions after meta-disubstitution has been achieved. And, depending upon the nature of these "additional reactions", it may be necessary to employ one or more protecting groups.

Hope the foregoing proves useful.

[mintyrogue]

Points to consider:

1. The product bears meta substituents. Thus, you must FIRST introduce a meta-directing substituent into the benzene ring.

2. When introducing the second substitutent, the chosen electrophile must either introduce an acetyl or hydroxymethyl group directly or, alternatively, introduce a suitable functional group that can serve as a precursor to one of the two groups present in the final product.

3. Depending on the method chosen to introduce substituents into the benzene ring, it may be necessary for to perform additional reactions after meta-disubstitution has been achieved. And, depending upon the nature of these "additional reactions", it may be necessary to employ one or more protecting groups.

Hope the foregoing proves useful.

Hi,

If I were to add NO₂ ortho to the ketone, would that work as a meta director? How would I remove the NO₂ group afterwards?

Also, to add the alcohol group, is it possible to use FC Acylation and then reduce the Ketone with LiAlH₄ to get an alcohol?

Thank you!

[orgopete]

While nitro is a meta director, it also deactivates a ring so Friedel-Crafts acylation fails. I suggest you reverse the order and possible second reaction.

[Demosthenes]

Hello,

So if we do the Friedel Crafts Acylation first, which gets us the carbonyl group, which is also a meta director so we're set there. I'm stumped on adding the second group, I know that if we can get an ester on it we can reduce it while protecting the ketone. But I don't know how to do that. Fisher Esterfication seems to be out as based on my notes, I'd have to already have an alcohol on the ring, which is what I'm trying to do. The only other groups I can think that can be converted are carboxylic acids and aldehydes/ketones.

Thank you!

[lrisNil]

Make the   following   compound from benzene. Show all   steps and   reagents.

Please be thorough, all help appreciated!

I'm also having trouble after performing FC Acylation, I can't figure out how to add the CH2OH 

[Demosthenes]

Alright, I have a solution of sorts. But I really don't like it, it feels overly convoluted and I'm pretty sure at least one step won't work.
Benzene to start
Step 1. Friedel Crafts Acylation FeCl₃ + methanoyl chloride
Step 2. Oxidation, H₂CrO₄
Alternately, any other method of making Benzoic Acid
Step 3. Fisher Esterification, H₃O⁺ + any alcohol
Now this next step I really don't like, although we have a meta directing carboxylic acid, the ring is also deactivated so I feel like the addition wouldn't work, but then that would happen with any meta director, so....
Step 4. Another Friedel Crafts Acylation FeCl₃ + ethanoyl chloride
Step 5. Adding a protective Group. H₃O⁺ + Ethylene Glycol
Step 6. Reduction, LiAlH₄ + H₃O⁺
Step 7. Back to the ketone, H₃O⁺

[chr147]

I am wondering why you want to do a fisher esterification? If you do a FC acylation, and then oxidize, wouldn't you then just add another acylation in the meta position? I am under the impression that you can still do the acylation because the COOH is moderately deactivating, not strongly deactivating (and it has to be strongly deactivating for the acylation not to occur)?

[orgopete]

It is difficult for us to guess THE route that is anticipated as we don't know the arsenal of reactions that have been covered. However, it does look like protection-deprotection and Grignard reactions may have been covered in addition to Friedel-Crafts reactions.

[Babcock_Hall]

Work backward.  Can you think of something that can be converted into the -OH group?

[lrisNil]

Thank you everyone, your posts were extremely helpful. I ended up doing FC Acylation first, then adding a methyl in the Meta position using FC Alkylation, then using a protecting group, and changing the methyl into CH2OH with LiAlH4 , I hope it's correct!

[Babcock_Hall]

I don't see how that last transformation would work.  Think backwards from the hydroxyl group.  What functional group do you know of that could be converted into an alcohol.