Gaylord
Chemical Company's
Comparative
Reaction Solvent Research
investigates
the Wittig Reaction
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
Wittig
reaction
is one
of the important reactions which we have evaluated. This
reaction
proceeds through the addition of phosphorus ylides to suitable carbonyl.
This is one of the preferred synthetic routes to produce alkenes. There are
two
steps to this reaction. The first typically involves de-protonation of a triphenylphos-
phonium halide, followed by addition of the intermediate ylide to a carbonyl.
Elimina-
tion of triphenylphosphine oxide provides the alkene product..
GCC
has investigated the
yields obtained using
DMSO for a series of hin-
dered cyclohexanones. At
right is an example where
DMSO use provides the
highest yields:
Ph
3
PCH
3
I
Ph
3
P
CH
2
O
Ph
3
P
CH
2
DMSO
NaCH
2
S(O)CH
3
R. Greenwald,
M. Chaykovsky, and E.J. Corey, J. Org. Chem. 28, 1128 (1963).
DMSO
0
10
20
30
40
50
60
70
80
90
100
DMSO
THF
NMP
DMF
98
51.1
87.3
45.5
%
Y
i
e
l
d
O
CH
2
Ph
3
P CH
2
solvent
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 Wittig Reaction
D
M S O
Bulletin
152B
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