Re: ORGLIST: Everybody Digest, Vol 35, Issue 5

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From: Anand Pandey (anand.pandey$##$alembic.co.in)
Date: Wed Jun 06 2007 - 23:46:56 EDT


Dear Dr. Rajasekharan,
The bromination of Acetyl group can be done with bromine in
chloroform/ethers as solvents in the presence/absence of lewis acid as
catalyst(very little qty). The rate of addition of bromine should be
very slow. You can also check the cross ref of phenacyl bromide.
Hope! this will work.
Regards
ANAND PANDEY

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Subject: Everybody Digest, Vol 35, Issue 5

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Today's Topics:

   1. bromination (kallikat rajasekharan)
   2. Re: Neutralizing TLC plates? (will jones)
   3. help (nanjundaswamy swamy marisetty)
   4. Re: Neutralizing TLC plates? (Ohad Ilovich)

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

Message: 1
Date: Tue, 5 Jun 2007 09:31:09 -0700 (PDT)
From: kallikat rajasekharan <rajkn_1951$##$yahoo.com>
Subject: ORGLIST: bromination
To: orglist <everybody$##$orglist.net>
Message-ID: <922952.40636.qm$##$web61124.mail.yahoo.com>
Content-Type: text/plain; charset=iso-8859-1

Hi all:

I need to brominate the acetyl group of
4-acetyl-2,6-di-t-butylphenol
[3,6-di-t-butyl-4-hydroxyacetophenone]. Tried bromine
in ether with/without light or AlCl3 and also with
CuIIBr2 in EtOAc. Only partial bromination. One
russian patent mentions bromination at 120 oC in
n-octane under light bulb. Any
alternatives/suggestions?
Thanks in advance

KN Rajasekharan PhD
Prof Chem
Univ Kerala

 
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Message: 2
Date: Tue, 05 Jun 2007 17:18:04 +0000
From: "will jones" <willjones46$##$hotmail.com>
Subject: Re: ORGLIST: Neutralizing TLC plates?
To: bvogel95$##$gmail.com, esprcorn$##$hotmail.com
Cc: everybody$##$orglist.net
Message-ID: <BAY132-F21CD8E65B3CE14604A824DAE200$##$phx.gbl>
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Brandon,

You aren't a relation to the legend Vogel, who wrote the best practical
organic chemistry book ever are you...?

Will

>From: "Brandon M. Vogel" <bvogel95$##$gmail.com>
>To: Ken Knott <esprcorn$##$hotmail.com>
>CC: everybody$##$orglist.net
>Subject: Re: ORGLIST: Neutralizing TLC plates?
>Date: Wed, 11 Apr 2007 23:12:11 -0400
>
>Ken Knott wrote:
> > I have a compound that I think may be degrading on TLC plates due to
> > the mild acidity.
> >
> > I would appreciate advice on how to neutralize TLC plates prior to
> > running them. I understand that this can be done with a 1% solution
> > of TEA in your eluent prior to running the compound? Can anyone
offer
> > any suggestions or advice on doing this?
> >
> > Also, how might I make myself more certain that I am in fact
> > witnessing degradation of my compound as a result of running it on
the
> > TLC?
> >
> > Thanks in advance!
> >
> > Ken
> >
> >
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>You may try passivating the TLC plate with hexamethyl disilazane (HMDS)
>via a vapor treatment. This procedure will methylate the SiO2. Of
>course, you will also have to functionalize your SiO2 if you run a
column.
>
>
>Brandon

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Message: 3
Date: 6 Jun 2007 02:51:01 -0000
From: "nanjundaswamy swamy marisetty" <jrchemist_1999$##$rediffmail.com>
Subject: ORGLIST: help
To: everybody$##$orglist.net
Message-ID: <20070606025101.15133.qmail$##$webmail34.rediffmail.com>
Content-Type: text/plain; charset="iso-8859-1"

Dear all,
Please suggest me to reduce picric acid to 2,4,6-triamino phenol
Thanks in advance,
H M Nanjundaswamy
PHI
Bangalore?
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Message: 4
Date: Wed, 6 Jun 2007 07:20:07 +0200
From: "Ohad Ilovich" <ilovich$##$pob.huji.ac.il>
Subject: Re: ORGLIST: Neutralizing TLC plates?
To: <everybody$##$orglist.net>
Message-ID: <001801c7a7fa$58d70e60$0e33a8c0$##$CYCLO14>
Content-Type: text/plain; charset="iso-8859-8"

Great idea Jason
I'll have to remember that trick for future use....
btw i've seen people running the whole TLC with 1% TEA and no just
washing the silica beforehand with it to keep their materials stable. it
hampers the TLC visualization in some systems but it does work with acid
sesitive materials
Ohad
  ----- Original Message -----
  From: JASON SMITH
  To: everybody$##$orglist.net
  Sent: Tuesday, June 05, 2007 8:54 AM
  Subject: Re: ORGLIST: Neutralizing TLC plates?

  Stability on silica can be checked by running a 2D TLC:

  Using a square silica plate, spot the sample in one corner.

  ? Run the plate in one direction (all components of the sample will
appear in a vertical line of spots).

  ? Turn the plate 90 degrees (your "line of spots" should be at the
bottom) and run the plate again.

  ? If the sample is stable to silica, all spots will appear on the
diagonal.

  -Jason

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

  Ken Knott wrote:
    I have a compound that I think may be degrading on TLC plates due to
the mild acidity.

    I would appreciate advice on how to neutralize TLC plates prior to
running them. I understand that this can be done with a 1% solution of
TEA in your eluent prior to running the compound? Can anyone offer any
suggestions or advice on doing this?

    Also, how might I make myself more certain that I am in fact
witnessing degradation of my compound as a result of running it on the
TLC?

    Thanks in advance!

    Ken

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unsubscribe your_orglist_password your_addressYou may try passivating
the TLC plate with hexamethyl disilazane (HMDS) via a vapor treatment.
This procedure will methylate the SiO2.  Of course, you will also have
to functionalize your SiO2 if you run a column.

Brandon

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