Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2004(9): 1604-1606
DOI: 10.1055/s-2004-829058
DOI: 10.1055/s-2004-829058
LETTER
© Georg Thieme Verlag Stuttgart · New York
Environmentally Friendly Esterification of Carboxylic Acids with Triethyl Orthoacetate in Ionic Liquid
Further Information
Received
19 March 2004
Publication Date:
29 June 2004 (online)
Publication History
Publication Date:
29 June 2004 (online)
Abstract
An operationally simple, inexpensive, efficient, and environmentally friendly esterification of carboxylic acids with triethyl orthoacetate under neutral conditions in a typical room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate, was carried out to provide the corresponding ethyl esters in high yields.
Key words
carboxylic acid - ethyl ester - triethyl orthoacetate - ionic liquid - environmentally friendly
- 1
Fischer E.Speier A. Ber. 1895, 28: 3252 -
2a
Beaz G. Comprehensive Organic Synthesis Vol. 6:Trost BM.Fleming I. Pergamon; Oxford: 1991. -
2b
Protective Groups in Organic Synthesis
3rd ed.:
Greene TM.Wutz PG. Wiley; New York: 1999. -
2c
Otera J. Chem. Rev. 1993, 93: 1449 - Reviews:
-
3a
Welton T. Chem. Rev. 1999, 99: 2071 -
3b
Wasserscheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 -
3c
Sheldon R. Chem. Commun. 2001, 2399 -
3d
Sheldon RA. Pure Appl. Chem. 2000, 72: 1233 -
3e
Earle MJ.Seddon KR. Pure Appl. Chem. 2000, 72: 1391 -
3f
Zhao H.Malhotra SV. Aldrichim. Acta 2002, 35: 75 -
4a
Surette JKD.Green L.Singer RD. Chem. Commun. 1996, 2753 -
4b
Adams CJ.Earle MJ.Roberts G.Seddon KR. Chem. Commun. 1998, 2097 -
5a
Monteiro AL.Zinn FK.De Souza RF.Dupont J. Tetrahedron: Asymmetry 1997, 8: 177 -
5b
Dyson PJ.Ellis DJ.Parker DG.Welton T. Chem. Commun. 1999, 25 -
5c
Adams CJ.Earle MJ.Seddon KR. Chem. Commun. 1999, 1043 -
6a
Howarth J.Hanlon K.Fayne D.McCormac P. Tetrahedron Lett. 1997, 38: 3097 -
6b
Huddleston JG.Rogers RD. Chem. Commun. 1998, 1765 -
6c
Lee CW. Tetrahedron Lett. 1999, 40: 2461 -
7a
Carmichael AJ.Earle MJ.Holbrey JD.McCormac PB.Seddon KR. Org. Lett. 1999, 1: 997 -
7b
Calo V.Nacci A.Lopez L.Mannarini N. Tetrahedron Lett. 2000, 41: 8973 -
7c
Mathews CJ.Smith PJ.Welton T. Chem. Commun. 2000, 1249 -
7d
Fukuyama T.Shinmen M.Nishitani S.Sato M.Ryu I. Org. Lett. 2002, 4: 1691 -
7e
Mayo KG.Nearhoof EH.Kiddle JJ. Org. Lett. 2002, 4: 1567 - 8
Calo V.Nacci A.Lopez L.Lerario VL. Tetrahedron Lett. 2000, 41: 8977 -
9a
Owens GS.Abu-Omar MM. Chem. Commun. 2000, 1165 -
9b
Howarth J. Tetrahedron Lett. 2000, 41: 6627 -
9c
Ansari IA.Gree R. Org. Lett. 2002, 4: 1507 -
9d
Yanada R.Takemoto Y. Tetrahedron Lett. 2002, 43: 6849 -
9e
Liu Z.Chen Z.-C.Zheng Q.-G. Org. Lett. 2003, 5: 3321 -
10a
Morrison DW.Forbes DC.Davis JH. Tetrahedron Lett. 2001, 42: 6053 -
10b
Xie Y.-Y.Chen Z.-C.Zheng Q.-G. Synthesis 2002, 1505 -
10c
Su C.Chen Z.-C.Zheng Q.-G. Synthesis 2003, 555 - 11
Ren RX.Zueva LD.Ou W. Tetrahedron Lett. 2001, 42: 8441 -
12a
Deng Y.Shi F.Beng J.Quio K. J. Mol. Cat. A.: Chem. 2001, 165: 33 -
12b
Fraga-Dubreuil J.Bourahla K.Rahmouni M.Bazureau JP.Hamelin J. Cat. Commun. 2002, 3: 185 -
12c
Brinchi L.Germani R.Savelli G. Tetrahedron Lett. 2003, 44: 2027 -
13a
Kim DW.Song CE.Chi DY. J. Am. Chem. Soc. 2002, 124: 10278 -
13b
Chiappe C.Pieraccini D.Saullo P. J. Org. Chem. 2003, 68: 6710 -
13c
Brinchi L.Germani R.Savelli G. Tetrahedron Lett. 2003, 44: 6583 -
13d
Brinchi L.Germani R.Savelli G. Tetrahedron Lett. 2003, 44: 2027 -
13e
Mohile SS.Potdar MK.Salunkhe MM. Tetrahedron Lett. 2003, 44: 1255 -
13f
Yadav JS.Reddy BVS.Basak AK.Venkat Narsaiah A. Tetrahedron Lett. 2003, 44: 2217 -
13g
Kotti SRSS.Xu X.Li G.Headley AD. Tetrahedron Lett. 2004, 45: 1427 - 14
Togo H.Hirai T. Synlett 2003, 702 -
15a
Hurd CD.Pollack MA. J. Am. Chem. Soc. 1938, 60: 1905 -
15b
MacKenzie CA.Stocker JH. J. Org. Chem. 1955, 20: 1695 -
15c
Wohl RA. Synthesis 1974, 38 -
15d
Patwardhan SA.Dev S. Synthesis 1974, 348 -
15e
Taylor EC.Chiang C.-S. Synthesis 1977, 467 -
16a
Padmapriya AA.Just G.Lewis NG. Synth. Commun. 1985, 15: 1057 -
16b
Trujillo JI.Gopalan AS. Tetrahedron Lett. 1993, 34: 7355
References
Most ethyl esters were identified by comparison with authentic commercially available materials, or with spectroscopic and microanalytical data.