Free accessResearch articleFirst published online 2000-6
A Simple Method for the Preparation of Monomethyl Esters of Dicarboxylic Acids by Selective Esterification of the Nonconjugated Carboxyl Group in the Presence of an Aromatic or Conjugated Carboxyl Group †
Various dicarboxylic acids have been converted selectively into monomethyl esters in which the nonconjugated carboxyl group is selectively esterified in the presence of an aromatic or conjugated carboxyl group at room temperature (~ 25–27° C) in methanol using a catalytic amount of thionyl chloride.
References
1.
(a) LarockR.C., Comprehensive Organic Transformations, VCH Publishers, Inc.: New York, 1989, p. 966.
2.
GreenT.W., and WutsP. G. M., Protective groups in organic synthesis; 2nd Ed.; Wiley: New York, 1991, p. 224
3.
OgliarusoM.A., and WolfeJ. F., Synthesis of Carboxylic Acids And Their Derivatives; PataiS., and RappoportZ., Eds.; John Wiley & Sons, Inc.: New York, 1991, pp. 145–148.
4.
(a) RamR. N., and CharlesI., Tetrahedron, 1997, 53, 7335 and references cited therein.
5.
RodriguezA., NomenM., SpurB. W., and GodfroidJ. J., Tetrahedron Lett., 1998, 39, 8563.
6.
AnandR.C., Vimal, and MilhotraA., J. Chem. Res. (S)1999, 378.
7.
HosangadiB.D., and DaveR. H., Tetrahedron Lett., 1996, 37, 6375.
8.
BanerjeeA., AdakM. M., DasS., BanerjeeS., and SenguptaS., J. Ind. Chem. Soc., 1987, 64, 34.
9.
BakerB.R., SchaubR. E., and WilliamsJ. H., J. Org. Chem., 1952, 17, 116.
10.
GrummitO., EganR., and BuckA., Org. Synth., Coll., 1955, 3, 449.
11.
BalaceanuJ.C., and de RadzitzkyP., Brit. 778,311, July 3, 1957; Chem Abstr.1958, 52, 1245.
12.
CodingtonJ.F., and MosettigE., J. Org. Chem., 1952, 17, 1035.
