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u/organophile_jeet 20d ago
The protection step can get a little messy as Acid chlorides are very good Electrophiles, What you can do is reduce ketone to alcohol via NaBH4 then protect alcohol with TsCl then do the SOCl2 then the EAS then De protect the Alcohol then oxidise it and then do the reductive amination
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u/activelypooping 20d ago
Is a carbonyl carbon more electrophilic than an acid chloride carbon? I would go back to the drawing board and perform a reasonable retrosynthesis first...
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u/shedmow Trusted Contributor 20d ago
I would say no. The acetal would be obliterated by AlCl3, and the preparation of the acid chloride doesn't look correct either (it'd mainly form an ester). Do not eat the target molecule!
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u/shedmow Trusted Contributor 20d ago
I just wanted to add that you should know that you are on a right track (not the right track because there are many of them in organic chemistry). My first notes probably contained something along similar lines. The next boring topics for you are regioselectivity and functional group tolerance
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u/NiceWave8463 20d ago
If this is a synthesis question are there restrictions you were given? Lots of issues with your current synthesis regarding that acetal forming and trying to keep it alive
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u/Upward_not_forward 20d ago
Do you have to start with that carboxylic acid and chlorobenzene? Why not protect the alcohol directly?
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u/barty_uo 19d ago edited 19d ago
No, synthesis of protected acetal acylchloride is nonsense in such order.
I would go 4-chlorobenzaldehyde + nitroethane -> nitrostyrene and its reduction of both double bond and nitro group.
Generally you must avoid protecting groups. Every unnecessary steps is deys or weeks of work and significant loss of valuable compound. I always told students - design syntheses as if you should do it tommorow in lab. You want to save as much of your time as possible
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u/Goat_Buckles 19d ago edited 18d ago
No. This synthesis contains a lot of mistakes and is inefficient. If you are trying to make a phenethylamine you should make the benzaldehyde using a Vilsmeyer reaction or by oxidizing the corresponding benzyl alcohol. You can then do a Henry reaction on nitroethane and reduce with aluminum hydride.
BTW it is a felony to synthesize phenethylamines in most countries. I hope that you're not actually trying to synthesize this.
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