PrimoPyro (Hive Prodigy)
04-15-02 17:11
No 297415
      Cyclohexyl-Acetone Dehydrogenation?  Bookmark   

TFSE doesn't like my terminology on this one apparantly. I can't find any previous discussions on this topic.

Has anyone ever considered dehydrogenating 1-cyclohexyl-2-propanone to form 1-phenyl-2-propanone/P2P?

Wouldn't copper chromite and oxygen promote such a dehydrogenation quite well? This would be awesome, because it's only one step away from P2P and dehydrogenation yields are often closely related to reaction times. SWIPP has never had any problems with the idea of letting a reaction go on for 30 hours if that's what the procedure calls for.

Perhaps refluxing toluene as solvent, so azeotropic removal of water as it is formed, by a Dean Stark type water trap?

Cyclohexylacetone is CASRN# [000103-78-6] just to add the info to the database. Chemfinder does not have it in it's database.


Vivent Longtemps La Ruche!
(Chief Bee)
04-15-02 17:45
No 297436
      dehydrogenation  Bookmark   

I believe the dehydrogenation of the nasal decongestant cyclohexyl-2-(methylamino)-propane has been discussed before, and it is quite similar in structure.
(Hive Bee)
04-15-02 19:03
No 297460
      Hard conditions  Bookmark   

A quick beilstein search gave 2 hits (they are making alkyl-benzen) The conditions are pt/on asbethos at 400C I don't think that the ketone(or alcohol) will survive that
(Hive Prodigy)
04-15-02 19:18
No 297468
      I See.  Bookmark   

Rhodium: Thank you, I did not know this compound was used for this purpose.

hest: Thank you as well, this is exactly the type of information I sought. I appreciate your reply immensely.

Because of such harsh conditions, this reaction doesn't seem to be a viable option for P2P synthesis, and most certainly not for MDP2P, because the needed starting compound is very hard to manufacture, and the harsh conditions would likely destroy the ring anyway.

Now I see why this hasn't been discussed. laugh


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