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All 5 posts Subject: Mg(MeO)2 route to benzaldehydes Please login to post Down

lutesium
(Stranger)
07-19-04 20:49
No 520322
      Mg(MeO)2 route to benzaldehydes

After following the patent for formylation w/ Mg(MeO)2, my friend was left w a yellowish oil. All chemicals were reag. grade(except p-meophenol. But it was crystallyzed twice and were white, 5-7 cm needles. They can also be assumed as reag. grade.) and the scale was 3g p-meo phenol. is skilled at practical synthetic chemistry.

Everything went an its writtten in the patent to the last second, but after the evaporation of toluene he was left with a pale yellow oil whose identitiy was unknown to him as he was hoping for cs crystallyne solid. Is this 2-OH-4-MeO-Bzaldehyde or did he screw up the rxn.

Vitus_Verdegast
(Hive Addict)
07-19-04 20:56
No 520324
User Picture       ahem..

NO this is NOT 2-OH-4-MeO-Bzaldehyde!!!

_{...but 2-OH-5-MeO-benzaldehyde!}

Yes, a yellow oil with a pleasant smell is what you should have. Interesting to see that you obtained what seems like a reasonably pure product from it, making the cumbersome steam-distillation process unnecessary.

How do you plan to alkylate it?

http://www.mindspring.com/~rathcoombe/horror/raven2.jpg

lutesium
(Stranger)
07-20-04 00:08
No 520356
      thanx vitus!

That made me feel better to hear that thay lovely yellow oil is what I want :)
(I reccomend this Mg(MeO)2 route to anybody. Ist easy and high yielding. Thanx to other bees who posted the method and saved me from the messy low yield reimerr-tiemann.)

I plan alkylatin w/ MeI followed by reduction to the alcohol - halogenation of the benzylic -oh then reacting it w/cyanide and reduction w/ Na metal.

I know that Its a long long long process but I have no access to R-NO2 s to form a nitrostyrene which I REALLY would like to :(

btw does anybody know if p-methoxyphenol dissolves in benzene?

GC_MS
(Hive Addict)
07-20-04 07:08
No 520385
User Picture       RT

Reimer-Tiemann is not low-yielding (at least for p-methoxyphenol), only messy. Considering the necessary precursor (water, chloroform and NaOH), I think this is still a method worthy of some respect wink .

Also, how did you purify your end product? Did you obtain the pale oil after you removed toluene by distillation, or did you distill the benzaldehyde? On several occasions, I obtained a yellow oil after I removed toluene by distillation. When I wanted to purify the oil, there was a very pale yellow oil comming over before 2-hydroxy-5-methoxybenzaldehyde. I cannot remember at what temperature (but more than toluene) and - as usual - can't find my notes crazy . The very pale yellow oil has an odour very different from toluene though. The benzaldehyde mixture turns into black. Further increasing the temperature will furnish me the benzaldehyde as a pale yellow oil, pleasantly odouring and staining my hands yellow.

Aztecunnilingus Maximus

lutesium
(Stranger)
07-21-04 00:50
No 520504
      GC_MS : I obtained the oil after the ...

GC_MS : I obtained the oil after the evaporation of toluene. It is crystal clear and smells a bit like toluene.
I would steam distill it but didnt bother as it was a very small scale rxn. But the yield of the undistilled aldehyde is nearly quantitative.

Edit: And I didnt mean disrespect to the reimer-tiemann. It has always been the bridge of my dreams up to now :)

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	All 5 posts		Subject: Mg(MeO)2 route to benzaldehydes		Please login to post		Down


		lutesium (Stranger) 07-19-04 20:49 No 520322				Mg(MeO)2 route to benzaldehydes
						After following the patent for formylation w/ Mg(MeO)2, my friend was left w a yellowish oil. All chemicals were reag. grade(except p-meophenol. But it was crystallyzed twice and were white, 5-7 cm needles. They can also be assumed as reag. grade.) and the scale was 3g p-meo phenol. is skilled at practical synthetic chemistry. Everything went an its writtten in the patent to the last second, but after the evaporation of toluene he was left with a pale yellow oil whose identitiy was unknown to him as he was hoping for cs crystallyne solid. Is this 2-OH-4-MeO-Bzaldehyde or did he screw up the rxn.



		Vitus_Verdegast (Hive Addict) 07-19-04 20:56 No 520324				ahem..
						NO this is NOT 2-OH-4-MeO-Bzaldehyde!!! _{...but 2-OH-5-MeO-benzaldehyde!} Yes, a yellow oil with a pleasant smell is what you should have. Interesting to see that you obtained what seems like a reasonably pure product from it, making the cumbersome steam-distillation process unnecessary. How do you plan to alkylate it? http://www.mindspring.com/~rathcoombe/horror/raven2.jpg



		lutesium (Stranger) 07-20-04 00:08 No 520356				thanx vitus!
						That made me feel better to hear that thay lovely yellow oil is what I want :) (I reccomend this Mg(MeO)2 route to anybody. Ist easy and high yielding. Thanx to other bees who posted the method and saved me from the messy low yield reimerr-tiemann.) I plan alkylatin w/ MeI followed by reduction to the alcohol - halogenation of the benzylic -oh then reacting it w/cyanide and reduction w/ Na metal. I know that Its a long long long process but I have no access to R-NO2 s to form a nitrostyrene which I REALLY would like to :( btw does anybody know if p-methoxyphenol dissolves in benzene?



		GC_MS (Hive Addict) 07-20-04 07:08 No 520385				RT
						Reimer-Tiemann is not low-yielding (at least for p-methoxyphenol), only messy. Considering the necessary precursor (water, chloroform and NaOH), I think this is still a method worthy of some respect . Also, how did you purify your end product? Did you obtain the pale oil after you removed toluene by distillation, or did you distill the benzaldehyde? On several occasions, I obtained a yellow oil after I removed toluene by distillation. When I wanted to purify the oil, there was a very pale yellow oil comming over before 2-hydroxy-5-methoxybenzaldehyde. I cannot remember at what temperature (but more than toluene) and - as usual - can't find my notes . The very pale yellow oil has an odour very different from toluene though. The benzaldehyde mixture turns into black. Further increasing the temperature will furnish me the benzaldehyde as a pale yellow oil, pleasantly odouring and staining my hands yellow. Aztecunnilingus Maximus



		lutesium (Stranger) 07-21-04 00:50 No 520504				GC_MS : I obtained the oil after the ...
						GC_MS : I obtained the oil after the evaporation of toluene. It is crystal clear and smells a bit like toluene. I would steam distill it but didnt bother as it was a very small scale rxn. But the yield of the undistilled aldehyde is nearly quantitative. Edit: And I didnt mean disrespect to the reimer-tiemann. It has always been the bridge of my dreams up to now :)

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