The acid catalyzed esterification of 2,6-dimethoxybenzoic acid ( 1) in the presence of absolute ethanol afforded ethyl 2, 6-dimethoxybenzoate ( 2). The structure of the resulting compound was supported by spectroscopic data and unambiguously confirmed by single crystal X-ray diffraction studies. The title compound crystallized in the triclinic space group P ī with unit cell parameters a = 8.5518(3) ?, b = 10.8826(8) ?, c = 11.9939(6) ?, α = 101.273(5)°, β = 98.287(3)°, γ = 94.092(4)°, V = 1077.54(10) ? 3, Z = 4, Dc = 1.296 Mg/m 3, F(000) = 448 and μ = 0.098 mm ?1. Compound ( 2) crystallizes with two molecules in the asymmetric unit with similar conformations.
References
[1]
Manjinder, S.L.; Yeeman, K.R.; Michael, N.G.J.; John, C.V. Serine and Threonine β-Lactones:A New Class of Hepatitis A Virus 3C Cysteine Proteinase Inhibitors. J. Org. Chem. 2002, 67, 1536–1547, doi:10.1021/jo0109016. 11871884
[2]
Tandon, V.K.; Yadav, D.B.; Singh, R.V.; Chaturvedi, A.K.; Shukla, P.K. Synthesis and activity of oleanolic acid derivatives, a novel class of inhibitors of osteoclast formation. Bioorg. Med. Chem. Lett. 2005, 15, 5324–5328, doi:10.1016/j.bmcl.2005.08.032.
[3]
Kumar, A.P.; Garcia, G.E.; Ghosh, R.; Rajnarayanany, R.V.; Alworth, W.L.; Slaga, T.J. 4-Hydroxy-3-Methoxybenzoic Acid Methyl Ester: A Curcumin Derivative Targets Akt/NFkB Cell Survival Signaling Pathway: Potential for Prostate Cancer Management. Neoplasia 2003, 5, 255–266. 12869308
[4]
Tomasz, Z.; Micha?, A.; Janusz, J. A simple synthesis of chiral macrocyclic tetraamides derived from α-amino acids. Tetrahedron: Asymmetry 2002, 13, 2053–2059, doi:10.1016/S0957-4166(02)00506-2.
[5]
Kim, J.; Kim, J.; Song, S.; Jung, O.; Suh, H. Enantiomeric Recognition of D- and L-Amino acidMethyl Ester Hydrochlorides by New Chiral Bis-pyridino-18-crown-6 Substituted with Urea, and Diphenyl Groups. J. Incl. Phenom.Macrocycl.Chem. 2007, 58, 187–192, doi:10.1007/s10847-006-9143-9.
Pollini, G.; Baricordi, N.; Benetti, S.; De Risi, C.; Zanirato, V. A simple entry to chiralnonracemic 2-piperazinone derivatives. Tetrahedron Lett. 2005, 46, 3699–3701, doi:10.1016/j.tetlet.2005.03.163.
[8]
Atsushi, N.; Toyoharu, M.; Hiroto, K.; Takeshi, E. Controlled Cationic Ring-Opening Polymerization of 1,3-Oxazolidine-2-thione Derived from L-Serine. Macromolecules 2003, 36, 9335–9339, doi:10.1021/ma030320d.
[9]
Khan, I.; Ali, S.; Hameed, S.; Rama, N.H.; Hussain, M.T.; Wadood, A.; Uddin, R.; Haq, Z.U.; Khan, A.; Ali, S.; Choudhary, M.I. Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Eur. J. Med. Chem. 2010, 45, 5200–5207, doi:10.1016/j.ejmech.2010.08.034. 20828889
[10]
Syed, T.; Akhtar, T.; Al-Masoudi, N.A.; Jones, P.G.; Hameed, S. Synthesis, QSAR and anti- HIV activity of new 5-benzylthio-1,3,4-oxadiazoles derived from α-amino acids. J. Enzym. Inhib. Med. Chem. 2011, 26, 668–680, doi:10.3109/14756366.2010.546792.
[11]
Legrand, S.; Nordlander, G.; Nordenhem, H.; Borg-Karlson, A.K.; Unelius, C.R. Hydroxy-Methoxybenzoic Methyl Esters: Synthesis and Antifeedant Activity on the Pine Weevil, Hylobius abietis. Z. Naturforsch. 2004, 59b, 829–835.
[12]
Blustein, G.; Romagnoli, R.; Jaen, J.A.; Di Sarli, A.R.; del Amo, B. Zinc basic benzoate as eco-friendly steel corrosion inhibitor pigment for anticorrosive epoxy-coatings. Colloid. Surface. A 2006, 290, 7–18, doi:10.1016/j.colsurfa.2006.04.043.
[13]
Yun-Choi, H.S.; Kim, M.H.; Jung, K.H. Esters of Substituted Benzoic Acids as Anti thrombotic Agents. Arch. Pharm. Res. 1996, 19, 66–70, doi:10.1007/BF02976823.
[14]
You, Y.J.; Kim, K.; Nam, N.H.; Bang, S.C.; Ahn, B.Z. Alkyl and carboxylalkyl esters of 4′-demethyl-4-deoxypodophyllotoxin: synthesis, cytotoxic, and antitumor activity. Eur. J. Med. Chem. 2004, 39, 189–193, doi:10.1016/j.ejmech.2003.10.002.
[15]
Habulin, M.; Sabeder, S.; Knez, Z. Enzymatic synthesis of sugar fatty acid esters in organic solvent and in supercritical carbon dioxide and their antimicrobial activity. J. Supercrit. Fluid. 2008, 45, 338–345, doi:10.1016/j.supflu.2008.01.002.