From: Mauricio Esguerra (inaco$##$altavista.com)
Date: Sat Feb 26 2000 - 14:25:45 EST
Thank you very much to everyone in the list it your help has been very helpful.
Here are the answers I got.
From:
"Schuit, ing. R.C." <RC.Schuit$##$azvu.nl>
Date:
Wed, 23 Feb 2000 08:53:38 +0100
To:
Multiple recipients of list orglist
<orglist$##$dq.fct.unl.pt>
Subject:
RE: ORGLIST: Dodecanol from dodecyl bromide
Dear Mauricio,
Dissolve your dodecylbromide in EtOH/DMSO (70/100) and
add 3 eq. of NaOAc
and reflux for 18h. Checked by GC. When the
startingmaterial
(RX) is
disapeared cooled the mixture down and add 1 volume of
water. Extract with
Hexane/Et2O (1:1). Wash your organic fases with brine and
water, dry on
MgSO4 or NaSO4 and evaporate the solvent. Purify the
acetate
with flash
chromatography (2% EtOAc/hexane). You have now the pure
acetate.
Saponificate the acetate in 5% KOH/EtOH by refluxing voor
4h. Extract with
hexane/Et2O (1:1). Wash the extracts with brine and water,
dry and evaporate
the solvent. Purify with flash chromatography with 5%
EtOAc/hexane
Good luck!
Cheers,
Robert C. Schuit
_\\^//_
(`!O-0!')
-----------------------------ooO-(_)-Ooo--------------------------------
"If the left side of your brain controls the right side
of your
body, then only left handed people are in their right
mind."
========================================================================
"Schuit, ing. R.C." <RC.Schuit$##$azvu.nl>
Date:
Wed, 23 Feb 2000 08:53:38 +0100
To:
"'Mauricio Esguerra'" <inaco$##$altavista.com>,
"'Orglist Mailinglist'" <orglist$##$dq.fct.unl.pt>
Subject:
RE: ORGLIST: Dodecanol from dodecyl bromide
Dear Mauricio,
Dissolve your dodecylbromide in EtOH/DMSO (70/100) and
add 3 eq. of NaOAc
and reflux for 18h. Checked by GC. When the
startingmaterial
(RX) is
disapeared cooled the mixture down and add 1 volume of
water. Extract with
Hexane/Et2O (1:1). Wash your organic fases with brine and
water, dry on
MgSO4 or NaSO4 and evaporate the solvent. Purify the
acetate
with flash
chromatography (2% EtOAc/hexane). You have now the pure
acetate.
Saponificate the acetate in 5% KOH/EtOH by refluxing voor
4h. Extract with
hexane/Et2O (1:1). Wash the extracts with brine and water,
dry and evaporate
the solvent. Purify with flash chromatography with 5%
EtOAc/hexane
Good luck!
Cheers,
Robert C. Schuit
_\\^//_
(`!O-0!')
-----------------------------ooO-(_)-Ooo--------------------------------
"If the left side of your brain controls the right side
of your
body, then only left handed people are in their right
mind."
=======================================================================
"Chapman, Robert D" <ChapmanRD$##$navair.navy.mil>
Date:
Wed, 23 Feb 2000 11:26:03 -0800
To:
Multiple recipients of list orglist
<orglist$##$dq.fct.unl.pt>
Subject:
ORGLIST: Dodecanol from dodecyl bromide
Here are some references to this general transformation
from my files, which
are by no means complete.
March, J. "Advanced Organic Chemistry" (4th ed.), p. 370;
Vogel, A.I. "Practical Organic Chemistry" (3rd ed.), pp.
247-249: though not
explicit, a straightforward route is suggested by the
examples
of reactions
of Grignard reagents, e.g., the Grignard from bromododecane
to be hydrolyzed
by water;
Larock, R.C. "Comprehensive Organic Transformations", p.
481, several
references;
Hutchins, R.O. J. Org. Chem. 1983, 48, 1360 (dodecanol
from bromododecane in
94% yield);
Gingras, M. Tetrahedron Lett. 1989, 279;
Alexander, J., Amer. Chem. Soc. 209th Nat. Meeting, April
1995, abstract
ORGN 277;
Patai & Rappaport, "The Chemistry of halides,
pseudo-halides
and azides,
Supplement D2", p. 718;
Ruddick, C.L. Synthesis 1996, 1359;
Sawamura, M. Chem. Lett. 1997, 705.
Robert D. Chapman, Ph.D.
Chemistry & Materials Division (Code 4T4200D)
Naval Air Warfare Center Weapons Division
China Lake, CA 93555 USA
From:
Jonas Nilsson <jonni$##$ifm.liu.se>
Try:
Hutchins, Robert O.; Taffer, Ira M.; J.Org.Chem.; EN; 48;
8; 1983; 1360-1362;
The reaction you are looking for is described in this
article
======================================================
From:
Uno Maeorg <uno$##$chem.ut.ee>
Date:
Tue, 22 Feb 2000 20:17:03 +0200 (EET)
To:
Mauricio Esguerra <inaco$##$altavista.com>
Subject:
Re: ORGLIST: Dodecanol from dodecyl bromide
Hi Mauricio,
I dont know the exact source you asked, but I can recommend
to use two
step technology which can give you nearly quantitative
yield.
First you have to make the acetate with potassium carbonate
in boiling
DMF and then you have to hydrolyze the acetate without
separation. This
is the classics and you can give any monograph of organic
transformations
as a source.
Dr. Uno Maeorg
! e-mail
: uno$##$chem.ut.ee
University of Tartu, Institute of Organic Chemistry! phone
: +(3727)375243
2 Jakobi St, Tartu 50090, Estonia ! fax
: +(3727)375243
===========================================================
Mauricio,
Porque no checas el libro de Richard Larock?
Comprehensive Organic Synthesis, me parece que es el
titulo, en el, hay listas extensas de todo tipo de
transformación que necesites. Si tu quieres, voy a
darme una vuelta a nuestra biblioteca de investigación
y te lo busco. Si ya conseguiste la informacion que
necesitas, puedes ignorar este mensaje. Suerte en tu
proyecto.
Antonio Regla
From:
Daniel Trachsel <Daniel_Trachsel$##$gmx.ch>
Date:
Thu, 24 Feb 2000 07:45:25 +0100 (MET)
To:
Multiple recipients of list orglist <orglist$##$dq.fct.unl.pt>
Subject:
ORGLIST: Dodecanol from dodecyl bromide
Hi!
here s the good and easy way to synthesize your dodecanole
from
dodecylbromide!
Hutchins, Robert O.; Taffer, Ira M. in: J.Org.Chem.48;
1983; 1360-1362.
Solvent: H2O and HMPT, 5.5h, 1000C. Yield: 94%
hope I did help you.
greetings, daniel.
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Again
Thanks to all who responded!!!!!!!
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