Sciencemadness Discussion Board - a phenylpropyloxy ether

a phenylpropyloxy ether

Globey - 9-2-2009 at 19:56

OK, I can start again, and ask in the best way I know how. I'd like to construct a phenylpropyloxy ether using the alcohol, and was imagining I’d need 3-bromopropylbenzene to perform the alkylation (the ether would be the leaving group?), and HBr off the other end. So, I would imagine propylbenzene would be the 2ndary precursor (to 3-bromopropylbenzene, the primary), but I know this simple aromatic can also be used to make a controlled substance P2P, so I am leary of ordering it. Maybe someone has some helpful ideas on how I could accomplish this particular reaction without alarming anyone? Honestly, I could care less about amphetamines. It would just seem such a waste of time to have to synthesize such a simple chemical, propylbenzene. Is there an easier way to perform this alkylation? Thanks

[Edited on 9-2-2009 by Globey]

kclo4 - 9-2-2009 at 20:02

http://www.freechemsketch.com/

If you are having a hard time explaining what you want, as I noticed in your other thread, download chemsketch and draw the reaction or the molecule you have in mind.

Just an Idea

Sedit - 9-2-2009 at 20:03

Is this close to what your attempting to accomplish?

[Edited on 10-2-2009 by Sedit]

ether.JPG - 2kB

Globey - 9-2-2009 at 20:06

Quote:

Originally posted by Sedit
................

Is this close to what your attempting to accomplish?

[Edited on 9-2-2009 by Sedit]

Sedit,

sry, don't see anything but some banner saying "remote linking prohibited"

Sedit - 9-2-2009 at 20:11

Really sorry I didnt know that the picture shows up on my end.. How do I go about adding a picture then?

not_important - 9-2-2009 at 20:13

Quote:

Originally posted by Sedit
Really sorry I didnt know that the picture shows up on my end.. How do I go about adding a picture then?

Working for me, but the best way is to save the image on your computer, then use the "attachment" dialog at the bottom of the posting edit stuff to browse for that file.

Globey - 9-2-2009 at 21:21

Sedit, that would be it. Hopefully I more accurately described the problem: forming phenylpropyloxy ether using an alcohol. I read in Arctander that P2P actually could be reduced to propylbenzene, but that seems an awful lot of trouble to go through to get the desired molecule (and illegal to do without the proper license.) 1-Phenyl-2-nitropropene is not illegal, per se. Could it be used to go directly to propylbenzene? Also, was I right that I'll need something like bromoisocumene to do this, or might there be another way? Tnx

[Edited on 10-2-2009 by Globey]

Polverone - 9-2-2009 at 21:44

You'll get a lot further if you just ask your questions in a straightforward and clear way and stop talking about controlled substances and legality. It adds nothing to the substance of your inquiry. If you can't discuss such a simple molecule without constantly mentioning its nefarious relationship to other molecules that you wish to avoid, it gives precisely the opposite idea about your intentions.

chemrox - 9-2-2009 at 22:30

I read a comment in the locked thread you started that suggested you work on communication skills. I second that wholeheartedly. I had written a reply to what I thought you were asking about and just now deleted it. Work on the language so we can understand what it is you're talking about. And as the man says, leave the legallities alone. If you're trying to make p2p some backassward way it will be obvious and the thread will be locked again. There are plenty of places on the net you can find out how to do that. It's not very interesting chemistry as a whole and not at all what this place is about.

Sedit - 9-2-2009 at 22:44

Quote:

Originally posted by Globey
Sedit, that would be it. Hopefully I more accurately described the problem: forming phenylpropyloxy ether using an alcohol. I read in Arctander that P2P actually could be reduced to propylbenzene, but that seems an awful lot of trouble to go through to get the desired molecule (and illegal to do without the proper license.) 1-Phenyl-2-nitropropene is not illegal, per se. Could it be used to go directly to propylbenzene? Also, was I right that I'll need something like bromoisocumene to do this, or might there be another way? Tnx

[Edited on 10-2-2009 by Globey]

Ok see that a pictures worth a thousand words....two thousand in your case

Why does it seem as though you are trying to make an ether synthesis into so many unnessasary steps?
Have you ever considered dehydration of the corresponding alcohols?

This will however prove to be problematic due to the formation of other side products but mainly just a tool for you to visualize ways of going about this without propylene benzene.

[Edited on 10-2-2009 by Sedit]

syn.bmp - 109kB

Nicodem - 10-2-2009 at 00:28

I still do not know what the question is. Globey, up to now you wrote only a single sentence that only roughly indicates what your problem might be. Apparently you want to do a Williamson ether synthesis using phenylpropylbromide (which one? there are 6 isomers of which 3 aliphatic bromides useful for such a reaction).

I highly suggest you to take Polverone's suggestion seriously. When someone spends only one sentence on explaining his question and whole paragraphs on talking about precursors to illegal substances it is obvious he is either a highly confused person or has some nefarious business in mind (or most likely both). In any case this is not tolerated here and will upset a whole lot of members. Also, when opening threads without providing a single reference or without properly explaining the topic, please do so in the Beginnings section where I'm moving this anyway.

Sedit, the ether in your first picture is a 2-phenylethyl one, not any of the phenylpropyl ones.

not_important - 10-2-2009 at 02:03

Phenyl magnesium halide + 1,3 propylene oxide ==> 1-phenyl-3-hydroxy-propane.

That is used in a Williamson ether synthesis with a methyl halide, tosylate, or what have you, to give the methyl ether. Keeping the propanol as alcohol reduces problems with elimination forming the alkene.

It might be possible to use the magnesium halo-alkoxide from the Grignard+epoxide reaction in the Williamson.

Globey - 10-2-2009 at 06:38

not_important: You both understood, and answered my question. Many thanks

The alcohol in question is otherwise labile, so the (above) scheme seems additionally elegant. Yup, I would go directly with the intermediate from the Grignard (not isolating). Wouldn't be so worried about forming a dbl. bond on the chain as I am about destroying the sensitive parts of the alcohol, but I suppose that is a concern in your typical ether (dehydration) synthesis. Thanks for the help

Nicodem - 10-2-2009 at 07:30

Quote:

Originally posted by not_important
Phenyl magnesium halide + 1,3 propylene oxide ==> 1-phenyl-3-hydroxy-propane.

Interestingly enough, oxetan (1,3 propylene oxide) can also be used in a Friedel-Crafts reaction with benzene to give the same product (JACS, 76 (1954) 2313-2314) in 71% yield, while the use of PhMgX with CuI as catalyst gives 52% yield (Tetrahedron Lett. (1979) 1503-1506).

Quote:

Originally posted by Globey
The alcohol in question is otherwise labile, so the (above) scheme seems additionally elegant. Yup, I would go directly with the intermediate from the Grignard (not isolating).

It only seems elegant because you haven't bothered to check the price of oxetan, which happens to be approximately 600-times more expensive than 3-phenylpropanol (which is ~50EUR/kg only). I hope that by "alcohol in question is otherwise labile" you don't mean 3-phenylpropanol, since this is anything but labile.
I have not understood the rest of your post so I can't comment, except repeat that you really, really should work on your communication skills.

Sedit - 10-2-2009 at 07:47

Quote:

Sedit, the ether in your first picture is a 2-phenylethyl one, not any of the phenylpropyl ones.

Yes your absolutly correct. Sorry about that I will fix it Asap.

~Sedit

chemrox - 10-2-2009 at 08:16

@NIcodem: which is more commonly used terminology, "phenylethyl" or "phenethyl"? I've seen both and am not sure which to use in searches at ACS, RSC or patent finder.

sparkgap - 10-2-2009 at 08:36

@CRX: "phenethyl" I commonly encounter more in the older literature. But there is no harm in doing searches for both "phenethyl" & "2-phenylethyl".

sparky (~_~)

Globey - 10-2-2009 at 09:38

Quote:

Snip...

Generic examples here were meant to illustrate general concepts. No one said that the prototype example reflected the actual reaction.

Sedit - 10-2-2009 at 10:14

Google ether synthesis. It brings up about 3 different synthesis on the first page alone although for you I feel Williamson synthesis to be your best way to go about it because something tells me that magnesium halides are going to be problematic for you.

Quote:

No one said that the prototype example reflected the actual reaction.

please do us all a favor and post the actual reaction reaction the so we dont spend days playing guessing games.

Globey - 10-2-2009 at 21:17

Snip...

Quote:

Originally posted by Sedit
something tells me that magnesium halides are going to be problematic for you.

Quote:

I've never had trouble under less than anhydrous conditions. And I'm not just talking a small seed of iodine, trick. Did you think you were clever with that insult?

Best to choose the high road, if ya know what I mean

Sedit - 10-2-2009 at 21:23

LOL touchy arn't you?

No I was trying to help you but if its unwanted I will just as well leave this threed of confusing rhetoric alone. Sorry to say but you have shown that you havent slightest Idea of simple ether synthesis and your telling me that the grignard is simple?
So no insult was intended but Im sure i could think of one if thats what you wish!

Globey - 11-2-2009 at 06:41

Quote:

Originally posted by Sedit
LOL touchy arn't you?

You know what, I think your last response was tailored to my last reply. Sort of like the person who takes a joke offensively, and then the joke teller says "just kidding, tjeeze! (as if they are the one who is offended)", but only after the response (but of course). I guess I must have the "dumb" sticker still stuck to parts of me...no offense

Now, if you want to have serious chemistry talk without personalizing things, I suggest you stop taking low ball stabs, and (now) start being honest.

Ebao-lu - 11-2-2009 at 07:36

Try alkylating of benzylgringard with methyl cellosolve tosylate, mesylate etc (methyl cellosolve should be a solvent), phenethyl gringard with methoxymethyl chloride(made from HCl, CH2O and MeOH)

Globey - 11-2-2009 at 08:17

^^^^^^^^is that supposed to be funny? hehehe

Ebao-lu - 11-2-2009 at 08:48

yes, because benzylchlorides suppose to be lachrymators))
by the way, why not to start from either 3-phenylpropanol(that Nicodem suggested) or cinnamic acid?

[Edited on 11-2-2009 by Ebao-lu]

Nicodem - 12-2-2009 at 00:26

Globey, trolling is not tolerated on this forum. I'm not sure you are doing it or purpose or you really are so confused and demented as you try to appear. In both cases, the sanction is the same, posting suspension.
I'm locking this thread.