From: Chapman, Robert D (ChapmanRD$##$navair.navy.mil)
Date: Wed Feb 23 2000 - 14:26:03 EST
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: Schuit, ing. R.C.
> Sent: Tuesday, February 22, 2000 11:53 PM
> To: Multiple recipients of list orglist
> 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."
>
>
>
> > ----------
> > From: Mauricio Esguerra
> > Sent: dinsdag 22 februari 2000 20:19
> > To: Multiple recipients of list orglist
> > Subject: ORGLIST: Dodecanol from dodecyl bromide
> >
> >
> > Hello
> >
> > I am an undergraduate chemistry student in Colombia South America. Right
> > now I am doing a project with one of my teachers and I need to get
> > dodecanol from dodecyl bromide. I have searched my university library
> > thoroughly and have not found any experimental book or information about
> > its process and yielding.
> > I would greatly appreciate anyone who can point me to good references on
> > this.
> > I have of course already searched at March, Vogel, Wagner, and others
> with
> > no success.
> >
> > Thank you very much.
> >
> >
> > --------------------------------------
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