The
Comparative
Reaction Solvent Research
at Gaylord
Chemical Company,,
L.L.C.
systematically compares DMSO performance versus other common solvents
in commercially important reactions. Using established references from the
chemi-
cal literature, our scientists test reaction systems to ascertain the yield,
selectivity,
and reaction rates of DMSO versus other solvents.
The
Dieckmann
Cyclization
is one
of the important reactions which we have evalu-
ated.
This reaction involves the base-catalyzed cyclization of dicarboxylic esters
to
give -ketoesters, the intramolecular equivalent of the Claisen condensation.
Gaylord
Chemical Company's
Comparative
Reaction Solvent Research
investigates
the Dieckmann Cyclization
DMSO
COOEt
COOEt
H
+
O
COOEt
NaCH
2
S(O)CH
3
We have
investigated the yields obtained using DMSO with dimsyl ion as the base
versus a traditional method employing toluene and sodium metal. The graph
below
displays one of the examples where the usage of DMSO provides significantly
higher yields:
0
10
20
30
40
50
60
70
80
90
100
DMSO
Toluene
Solvent
tested
%
y
i
e
l
d
99.7
66.1
solvent
COOEt
COOEt
H
+
O
COOEt
NaCH
2
S(O)CH
3
or
Na metal
Gaylord
Chemical Company,
L.L.C. (GCC) is the world's
leading provider of Dimethyl
Sulfoxide (DMSO) solutions.
Beginning in the early
1960's ,GCC has been dedi-
cated to the development of
new uses for DMSO. In or-
der to meet customer-specific
needs, GCC has pioneered
the development of multiple
grades of DMSO, including
DMSO USP.
Gaylord Chemical's solutions
-based approach has contrib-
uted to the development and
growth of industries including
pharmaceuticals, hydro-
carbons, electronics, poly-
mers, coatings, agricultural
chemicals, and industrial
cleaners.
Gaylord Chemical's head-
quarters are located in Slidell,
Louisiana with manufactur-
ing, research, and develop-
ment facilities in nearby
Bogalusa, Louisiana. GCC
remains the only producer of
DMSO in the Western Hemi-
sphere.
DMSO
PRODUCT INFORMATION BULLETIN
dimethyl
sulfoxide
and the Dieckmann Cyclization
D
M S O
Bulletin
150B
Oct
2007
Gaylord
Chemical Company, L.L.C.
Your
Global Leader For DMSO Solutions!
P.O.
Box 1209
Slidell,
LA 70459-1209 USA
1.800.426.6620
Office
1.985.649.0068
Fax
info@gaylordchemical.com