Synthesis 2014; 46(02): 263-268
DOI: 10.1055/s-0033-1340285
paper
© Georg Thieme Verlag Stuttgart · New York

Methyl Salicylate as a Selective Methylation Agent for the Esterification of Carboxylic Acids

Si Chen
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85462021   Email: luomm@scu.edu.cn
,
Lei Jia
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85462021   Email: luomm@scu.edu.cn
,
Xiaonan Li
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85462021   Email: luomm@scu.edu.cn
,
Meiming Luo*
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85462021   Email: luomm@scu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 16 August 2013

Accepted after revision: 28 October 2013

Publication Date:
26 November 2013 (online)


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

 
  • 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
    • 3a Pozsgay V. Org. Lett. 1999; 1: 477
    • 3b Gustavo J, Avila-Zàrraga RM. Synth. Commun. 2001; 31: 2177
    • 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
    • 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
    • 11a Chan TY. Hum. Exp. Toxicol. 1996; 15: 747
    • 11b Davis JE. J. Emerg. Med. 2007; 32: 63
  • 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