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Author: Subject: Can I do anything interesting with 4-dimethylamino-benzaldehyde?
Doc B
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[*] posted on 29-9-2012 at 18:14
Can I do anything interesting with 4-dimethylamino-benzaldehyde?


I don't know why I have it nor when I got it but I have a largish amount of 4-dimethylamino-benzaldehyde. Which looks like this...



In keep with my vaugeness both general and related specifically to this reagent, I don't know what to do with it. Has anyone out there got any suggestions of an interesting or useful purpose for it?

For example, can it be delaminated back to benzaldehyde?
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Doc B
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[*] posted on 30-9-2012 at 02:30


Would conversion to the aldehyde via FeCl catalysied acid hydrolysis be possible?
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tetrahedron
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[*] posted on 30-9-2012 at 04:33


Quote: Originally posted by Doc B  
can it be delaminated back to benzaldehyde?


maybe via diazotization with sodium nitrite (Sandmeyer) and subsequent hydrogenolysis..but the CHO group might interfere
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Nicodem
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30-9-2012 at 06:37
kristofvagyok
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[*] posted on 30-9-2012 at 07:03


Quote: Originally posted by Doc B  
Has anyone out there got any suggestions of an interesting or useful purpose for it?

For example, can it be delaminated back to benzaldehyde?


Making benzaldehyde is aint so easy from that.. The formyl group will get damaged much more earlier that the NMe2 will get off.

But I have used this with ccH2SO4 and methanol to detect indoles in my reaction, it will give a nice colorination if any indole is in it. It also works with amines as I remember, so it is pretty useful. Also a lot dyes are made from it.




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Lambda-Eyde
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[*] posted on 30-9-2012 at 07:50


Wikipedia has some information of relevance.



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