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Green and Simple Synthesis of p-Anisic acid and Other Analogs from Methyl Paraben
Corresponding Author(s) : Selvaraj Subbiah
Asian Journal of Chemistry,
Vol. 30 No. 1 (2018): Vol 30 Issue 1
Abstract
Synthesis of p-anisic acid from commercially available methyl paraben was obtained in good yield and performed the each steps in shorter duration is reported. The E-factor was evaluated for each step was 3.0 and 2.30 respectively without transition metals content in the waste disposal. The solvents used in each steps were completely recovered and recycled in the consecutive batches. This methodology was applied to the synthesis of p-ethoxy benzoic acid and p-propyloxy benzoic acid and the other derivatives from methyl paraben obtained in good yield.
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References
U. Straetmans, J. Janichen, W. Petersen, M. Kinder, C. Johnson and G. Reynolds, Concentrated, Aqueous Solutions of p-Methoxybenzoic acid for use in Cosmetic and Dermatologic Formulations US Patent 20060229291A1 (2006).
T.L. Gianetti, S.P. Annen, G. Santiso-Quinones, M. Reiher, M. Driess and H. Grützmacher, Angew. Chem. Int. Ed., 55, 1854 (2016); https://doi.org/10.1002/anie.201509288.
P.L. Anelli, C. Biffi, F. Montanari and S. Quici, J. Org. Chem., 52, 2559 (1987); https://doi.org/10.1021/jo00388a038.
A. Kioytokuwabara and I. Itoh, Synthesis, 1949 (2006); https://doi.org/10.1055/s-2006-942374.
J. Malineni, H. Keul and M. Möller, Dalton Trans., 44, 17409 (2015); https://doi.org/10.1039/C5DT01358E.
D. Chakraborty, C. Majumder and P. Malik, Appl. Organomet. Chem., 25, 487 (2011); https://doi.org/10.1002/aoc.1787.
E. Dalcanale and F. Montanari, J. Org. Chem., 51, 567 (1986); https://doi.org/10.1021/jo00354a037.
L. sancineto, C. Tidei, L. Bagnoli, F. Marini, E. Lenardão and C. Santi, Molecules, 20, 10496 (2015); https://doi.org/10.3390/molecules200610496.
C.E. Ballard, J. Chem. Educ., 87, 190 (2010); https://doi.org/10.1021/ed800054s.
P. Sathyanarayana, O. Ravi, P.R. Muktapuram and S.R. Bathula, J. Org. Biomol. Chem., 37, 9681 (2015); https://doi.org/10.1039/C5OB01569C.
Y.-L. Hu, D.-J. Li and D.-S. Li, RSC Adv., 5, 24936 (2015); https://doi.org/10.1039/C5RA02234G.
K.A. Aravindakumar, V. Venkateswarlu, R. Vishwakarma and S. Sawant, Synthesis, 47, 3161 (2015); https://doi.org/10.1055/s-0034-1381026.
J.J. Brunet, C. Sidot and P. Caubere, Tetrahedron Lett., 22, 1013 (1981); https://doi.org/10.1016/S0040-4039(01)82853-7.
M. Markovic, P. Lopatka, P. Koós and T. Gracza, Org. Lett., 17, 5618 (2015); https://doi.org/10.1021/acs.orglett.5b02840.
T. mita, K. Suga, K. Sato and Y. Sato, Org. Lett., 17, 5276 (2015); https://doi.org/10.1021/acs.orglett.5b02645.
R. Naik and M.A. Pasha, Synth. Commun., 36, 165 (2006); https://doi.org/10.1080/00397910500334165.
Y.W. Hu, L. Zuo, D.Y. Ye and W.H. Duan, Chin. Chem. Lett., 20, 1157 (2009); https://doi.org/10.1016/j.cclet.2009.04.028.
K.A. Fjare, Process for Preparation of p-Hydroxybenzoic Acid from p-Methoxytoluene, US Patent 4740614 (1988).
D.J.C. Constable, A.D. Curzons and V.L. Cunningham, Green Chem., 4, 521 (2002); https://doi.org/10.1039/B206169B.
R.A. Sheldon, Chem. Ind., 903 (1992).
P.T. Anastas and J.C. Warner, Green Chemistry: Theory and Practice, Oxford University Press (2000).