A Facile, Catalytic and Environmentally Benign Method for Esterification of Carboxylic Acids and Transesterification of Carboxylic Esters with Nearly Equimolar Amounts of Alcohols

Abstract

A practical and green chemical process for the esterification of carboxylic acids with alcohols and transesterification of carboxylic esters in good to excellent yields by using K₅CoW₁₂O₁₄·3H₂O (0.1 mol%) as catalyst is reported. The catalyst exhibited remarkable reusable activity.

Key words

esterification - transesterification - alcohols - carboxylic acids - reusable

References

• 1a Beaz G. In Comprehensive Organic Synthesis   Vol. 6:  Trost B. Fleming I. M. Pergamon; Oxford: 1991.  p.323 
• 1b Otera J. Esterification. Methods, Reactions and Applications   Wiley-VCH; Weinheim: 2003. 
• 1c Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   3rd ed.:  Wiley; New York: 1999.  p.369 
• 1d Patai S. The Chemistry Acid Derivatives   Vol. 1:  Wiley; New York: 1979.  p.267 
• 2 Rehn D. Ugi I. J. Chem. Res., Synop.  1977,  119 
• 3 Banerjee A. Sengupta S. Adak MM. Banarjee GC. J. Org. Chem.  1983,  48:  3106 
• 4 Banerjee A. Adak MM. Das S. Banarjee S. Senugupta S. J. Indian Chem. Soc.  1987,  64:  34 
• 5 Ram RN. Caarles I. Tetrahedron  1997,  53:  7335 
• 6 Rodriguez A. Nomen M. Spur BW. Godfroid JJ. Tetrahedron Lett.  1998,  39:  8563 
• 7 Breton GW. J. Org. Chem.  1997,  62:  8952 
• 8 Olah GA. Keumi T. Meidar D. Synthesis  1978,  929 
• 9a Franklin AS. J. Chem. Soc., Perkin Trans. 1  1998,  2451 
• 9b Franklin AS. J. Chem. Soc., Perkin Trans. 1  1999,  3537 
• 10 Wakasugi K. Misaki T. Yamada K. Tanabe Y. Tetrahedron Lett.  2000,  41:  5249 
• 11 Ranu BC. Dutta P. Sarkar A. J. Org. Chem.  1998,  63:  6027 
• 12a Otera J. Yano T. Kawabata A. Nozaki H. Tetrahedron Lett.  1986,  27:  2383 
• 12b Taber DF. Amedio JC. Patel YK. J. Org. Chem.  1985,  50:  3618 
• 12c Seebach D. Hungerbühler E. Naef R. Schnurrenberger D. Weidmann B. Züger MM. Synthesis  1982,  138 
• 12d Rehberg CE. Fischer CH. J. Am. Chem. Soc.  1944,  66:  1203 
• 12e Balaji BS. Saridharan M. Kumar R. Chanda B. J. Chem. Soc., Chem. Commun.  1996,  707 
• 12f Ponde DE. Deshpande VH. Bulbule VJ. Sudalai A. Gajare AS. J. Org. Chem.  1998,  63:  1058 
• 12g Krasik P. Tetrahedron Lett.  1998,  39:  4223 
• 12h Ishihara K. Ohara S. Yamamoto H. Science  2000,  290:  1140 
• 12i Xiang J. Toyoshoma S. Orita A. Otera J. Angew. Chem. Int. Ed.  2001,  40:  3670 
• 12j Baumhof P. Mazitschek R. Giannis A. Angew. Chem. Int. Ed.  2001,  40:  3672 
• 12k Xiang J. Orita A. Otera J. Adv. Synth. Catal.  2002,  344:  84 
• 12l Ishihara K. Hasegawa A. Yamamoto H. Synlett  2002,  1299 
• 13 Mukaiyama T. Shiina I. Chem. Lett.  1995,  141 
• 14 For the preparation of the catalyst, see: Bose DS. Narsimha Reddy AV. Rudra Das AP. Synthesis  2003,  1883