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-00000084.xml
Synthesis 2014; 46(02): 263-268
DOI: 10.1055/s-0033-1340285
DOI: 10.1055/s-0033-1340285
paper
Methyl Salicylate as a Selective Methylation Agent for the Esterification of Carboxylic Acids
Further Information
Publication History
Received: 16 August 2013
Accepted after revision: 28 October 2013
Publication Date:
26 November 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201402/lookinside/thumbnails/10.1055-s-0033-1340285-1.jpg)
Abstract
Methyl salicylate is a selective and inexpensive methylating agent for the esterification of carboxylic acids with a wide range of functional group tolerance. The intramolecular hydrogen bonds between the carboxylate and hydroxyl groups in methyl salicylate are essential for the transformation. Allyl, benzyl, methallyl, and propargyl salicylates can also be used as alkylating agents for the preparation of the corresponding alkyl carboxylates.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Otera J, Nishikido J. Esterification . 2nd ed. Wiley-VCH; Weinheim: 2010
- 2a Shaw JE, Kunerth DC. J. Org. Chem. 1974; 39: 1968
- 2b Pfeffer PE, Silbert LS. J. Org. Chem. 1976; 41: 1373
- 4a Minisci F, Vismara E, Fontana F. J. Org. Chem. 1989; 54: 5224
- 4b Chakraborti AK, Nandi AB, Grover V. J. Org. Chem. 1999; 64: 8014
- 5a Proctor LD, Warr AJ. Org. Process Res. Dev. 2002; 6: 884
- 5b Cuevas-Yaňez E, Garcìa MA, Mora MA, Muchowski JM, Cruz-Almanza R. Tetrahedron Lett. 2003; 44: 4815
- 6 White EH, Bum AA, Eitel DE. Org. Synth. Coll. Vol. V. John Wiley & Sons; London: 1973: 797
- 7a Mathias LJ. Synthesis 1979; 561
- 7b Mohacsi E. Synth. Commun. 1982; 12: 453
- 7c Widmer U. Synthesis 1983; 135
- 7d Ttujillo JL, Gopalan AS. Tetrahedron Lett. 1993; 34: 7355
- 7e Gibson FS, Park MS, Rapoport H. J. Org. Chem. 1994; 59: 7503
- 7f Lee Y, Shimizu I. Synlett 1998; 1063
- 7g Shieh WC, Dell S, Repič O. J. Org. Chem. 2002; 67: 2188
- 7h Dhakshinamoorthy A, Sharmila A, Pitchumani K. Chem. Eur. J. 2010; 16: 1128
- 7i Heller ST, Sarpong R. Org. Lett. 2010; 12: 4572
- 8a Pokier LA, Stoner GD, Shimkin MB. Cancer Res. 1975; 35: 1411
- 8b McCann J, Choi E, Yamasaki E, Ames BN. Proc. Natl. Acad. Sci. U.S.A. 1975; 72: 5135
- 9 Field L, Clark RD. Org. Synth. Coll. Vol. IV. John Wiley & Sons; London: 1963: 674
- 10 DeBoer TJ, Backer HJ. Org. Synth. Coll. Vol. IV. John Wiley & Sons; London: 1963: 250
- 12 Lapczynski A, Jones L, McGinty D, Bhatia SP, Letizia CS, Api AM. Food Chem. Toxicol. 2007; 45: S428
- 13a Helmbrook LA, Kenny JE, Kohler BE, Scott GW. J. Phys. Chem. 1983; 87: 280
- 13b Aparicio S, Alcalde R. Eur. J. Chem. 2010; 1: 162
- 14 Kuper JW, Perry DS. J. Chem. Phys. 1984; 80: 4640
- 15 Kametani T, Kigasawa K, Hiiragi H. Tetrahedron Lett. 1965; 6: 1817
- 16 Albaneze-Walker J, Bazaral J, Leavey T, Dormer PG, Murry JA. Org. Lett. 2004; 6: 2097
- 17 Kaganovsky L, Gelman D, Rueck-Braun K. J. Organomet. Chem. 2009; 695: 260
- 18 Hirashima S, Nobuta T, Tada N, Miura T, Itoh A. Org. Lett. 2010; 12: 3645
- 19 Wang XL, Liu RH, Jin Y, Liang XM. Chem. Eur. J. 2008; 14: 2679
- 20 Carbaugh AD, Vosburg W, Scherer TJ, Castillo CE, Christianson MA, Kostarellas J, Gosai SJ, Leonard MS. ARKIVOC 2007; (xii): 43
- 21 Ko EJ, Savage GP, Tsanaktsidis J. Org. Lett. 2011; 13: 1944
- 22 Narasimhan B, Mourya V, Dhake A. Bioorg. Med. Chem. Lett. 2006; 16: 3023
- 23 Kantam ML, Yaday J, Laha S, Srinivas P, Sreedhar B, Figueras F. J. Org. Chem. 2009; 74: 4608
- 24 Soldi RA, Oliveira AR. S, Barbosa RV, César-Oliveira MA. F. Eur. Polym. J. 2007; 43: 3671
- 25 Kuninobu Y, Ohta K, Takai K. Chem. Commun. 2011; 47: 10791
-
26 Sher M, Dang TH. T, Ahmed Z, Rashid MA, Fischer C, Langer P. J. Org. Chem. 2007; 72: 6284
- 27 Dzhuraev AD, Makhsumov AG, Zakirov UB, Nikbaev AT, Karimkulov K. Khim.-Farm. Zh. 1990; 24: 30 ; Chem. Abstr. 1990, 113, 204426