Re: ORGLIST: Problem of METHYL IODIDE - IODOLACTONIZATION

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From: Suraya Zulkepli (kinrara_16$##$yahoo.com)
Date: Fri Sep 26 2008 - 09:28:29 EDT


Dear all,

Thanx a lot for respond to my problems..Here I'm attached of my nmr file.Yes,I think I got the peak ofmethyl iodide based on the ratio 2.18 ppm from my spectrum..I think maybe coz I used the boiling point during rotavape only 41 celciuS..I used CDCl3 for nmr solvent..I used ethyl acetate solvent when I did PREP TLC.

Actually from this reaction I got 2 types of product.

I want to know is it the lactone product can be visualized under UV and Iodine vapor?Its because I can saw the product both of them.Is it lactone product is too sensitive to light and air ???Its because its like unstable product..

I think I got 6 membered ring but still wonder why the methoxy peak(3.68 ppm) is still there from the nmr result.(from file product1a)?? But from the file product 1b, no methoxy peak...why is it??

Hope anyone can help me..

THANX IN ADVANCE..:)

SURAYA

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Today's Topics:

   1. removal of methyl iodide (Mugunthan G)
   2. Re: How to separate methyl iodide (Hima Potturi)
   3. Re: How to separate methyl iodide (cardman)
   4. Re: How to separate methyl iodide (Sandra Bartoli)

----------------------------------------------------------------------

Message: 1
Date: Wed, 24 Sep 2008 21:50:52 +0530 (IST)
From: Mugunthan G <mugunthan_gee$##$yahoo.co.in>
Subject: ORGLIST: removal of methyl iodide
To: everybody$##$orglist.net
Message-ID: <668925.18691.qm$##$web8902.mail.in.yahoo.com>
Content-Type: text/plain; charset="utf-8"

hi suraya,
?????? I am surprised to hear that u can't separate methyl iodide from your desired product, methyl iodide is low boiling liquid (42.5 degree celcius) if u put it under vaccum it should disappear, sometimes even if u leave the flask open overnight next day it will be clean. Even after evaporating in a rotaevaporator , if u still get a methyl peak in NMR , i can say u it?s not because of methyl iodide
?

MUGUNTHAN.G
GLYCOCHEMISTRY LABORATORY?
DEPARTMENT OF MEDICINAL CHEMISTRY
NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH
SECTOR-67,PHASE-10, MOHALI
PUNJAB-160062
INDIA

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Message: 2
Date: Wed, 24 Sep 2008 12:15:24 -0500
From: "Hima Potturi" <himakp$##$siu.edu>
Subject: Re: ORGLIST: How to separate methyl iodide
To: <everybody$##$orglist.net>
Message-ID: <200809241714.m8OHEs9k023540$##$cstmta2.siu.edu>
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Methyl iodide has very low boiling point (around 42C). You should be able to
get rid of it on a rotovapor.

Date: Tue, 23 Sep 2008 23:12:21 -0700 (PDT)
From: Suraya Zulkepli <kinrara_16$##$yahoo.com>
Subject: ORGLIST: How to separate methyl iodide from the main product
    (IODOLACTONIZATION)
To: everybody$##$orglist.net
Message-ID: <583068.44937.qm$##$web53912.mail.re2.yahoo.com>
Content-Type: text/plain; charset="us-ascii"

Can anyone tell me how to separate the compund of methyl iodide from the
product of 6 membered ring lactone?Its because I got from Nmr result still
have peak of CH3I..I also tried many ratio with HEX:EA but still cant
separate coz its look like overlapp with the main product even I can look
one spot with TLC under UV and Iodine.( means 2 compound in one spot).

Hope anyone can help me so..

Thanx in advance

Suraya

------------------------------

Message: 3
Date: Wed, 24 Sep 2008 13:55:30 -0700 (PDT)
From: cardman <cardman400$##$yahoo.com>
Subject: Re: ORGLIST: How to separate methyl iodide
To: everybody$##$orglist.net, Hima Potturi <himakp$##$siu.edu>
Message-ID: <213868.94505.qm$##$web38702.mail.mud.yahoo.com>
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It's also doubtful that you are seeing any methyl iodide by TLC, since it's not UV active and simple alkyl halides usually can't be visualized with iodine vapor. Even if it were present, it would probably evaporate off the plate along with your spotting solvent.

--- On Wed, 9/24/08, Hima Potturi <himakp$##$siu.edu> wrote:

> From: Hima Potturi <himakp$##$siu.edu>
> Subject: Re: ORGLIST: How to separate methyl iodide
> To: everybody$##$orglist.net
> Date: Wednesday, September 24, 2008, 10:15 AM
> Methyl iodide has very low boiling point (around 42C). You
> should be able to
> get rid of it on a rotovapor.
>
> Date: Tue, 23 Sep 2008 23:12:21 -0700 (PDT)
> From: Suraya Zulkepli <kinrara_16$##$yahoo.com>
> Subject: ORGLIST: How to separate methyl iodide from the
> main product
> (IODOLACTONIZATION)
> To: everybody$##$orglist.net
> Message-ID:
> <583068.44937.qm$##$web53912.mail.re2.yahoo.com>
> Content-Type: text/plain; charset="us-ascii"
>
> Can anyone tell me how to separate the compund of methyl
> iodide from the
> product of 6 membered ring lactone?Its because I got from
> Nmr result still
> have peak of CH3I..I also tried many ratio with HEX:EA but
> still cant
> separate coz its look like overlapp with the main product
> even I can look
> one spot with TLC under UV and Iodine.( means 2 compound in
> one spot).
>
> Hope anyone can help me so..
>
> Thanx in advance
>
> Suraya
>
>
>
> _______________________________________________
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Message: 4
Date: Thu, 25 Sep 2008 11:30:57 +0200
From: Sandra Bartoli <sandy13_1$##$hotmail.com>
Subject: Re: ORGLIST: How to separate methyl iodide
To: <cardman400$##$yahoo.com>, <everybody$##$orglist.net>, Hima Potturi
    <himakp$##$siu.edu>
Message-ID: <BAY136-W38BE92E373260B557A5FE7C2440$##$phx.gbl>
Content-Type: text/plain; charset="iso-8859-1"

I agree. I really do not think what you see is Methyl Iodide.
It must be that a methyl residue is attached somewhere else in your molecule.
What ratio can you see from NMR? i mean, what ratio supposed CH3I/product can you estimate from NMR? What's the chemical shift? In which solvent?

Sandra Bartoli> Date: Wed, 24 Sep 2008 13:55:30 -0700> From: cardman400$##$yahoo.com> To: everybody$##$orglist.net; himakp$##$siu.edu> Subject: Re: ORGLIST: How to separate methyl iodide> > It's also doubtful that you are seeing any methyl iodide by TLC, since it's not UV active and simple alkyl halides usually can't be visualized with iodine vapor. Even if it were present, it would probably evaporate off the plate along with your spotting solvent. > > > --- On Wed, 9/24/08, Hima Potturi <himakp$##$siu.edu> wrote:> > > From: Hima Potturi <himakp$##$siu.edu>> > Subject: Re: ORGLIST: How to separate methyl iodide> > To: everybody$##$orglist.net> > Date: Wednesday, September 24, 2008, 10:15 AM> > Methyl iodide has very low boiling point (around 42C). You> > should be able to> > get rid of it on a rotovapor.> > > > Date: Tue, 23 Sep 2008 23:12:21 -0700 (PDT)> > From: Suraya Zulkepli <kinrara_16$##$yahoo.com>> > Subject: ORGLIST: How to separate methyl iodide from the> > main
 product> > (IODOLACTONIZA
TION)> > To: everybody$##$orglist.net> > Message-ID:> > <583068.44937.qm$##$web53912.mail.re2.yahoo.com>> > Content-Type: text/plain; charset="us-ascii"> > > > Can anyone tell me how to separate the compund of methyl> > iodide from the> > product of 6 membered ring lactone?Its because I got from> > Nmr result still> > have peak of CH3I..I also tried many ratio with HEX:EA but> > still cant> > separate coz its look like overlapp with the main product> > even I can look> > one spot with TLC under UV and Iodine.( means 2 compound in> > one spot).> > > > Hope anyone can help me so..> > > > Thanx in advance> > > > Suraya> > > > > > > > _______________________________________________> > ORGLIST - Organic Chemistry Mailing List> > Website / Archive / FAQ: http://www.orglist.net> > To post a message (TO EVERYBODY) send to> > everybody$##$orglist.net> > To unsubscribe, send to everybody-request$##$orglist.net the> > message: unsubscribe your_orglist_password your_address> >
> > _________________
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