Abstract
Acylation of 4-methoxy phenol according toFriedel andCrafts, as well as the rearrangement of its esters according toFries lead always to 2-acyl-4-methoxy phenols or to their demethylated compounds. The unknown 3-acyl-4-methoxy phenols were prepared in two steps: First, the ester is acylated with the corresponding acyl chloride and SnCl4 in nitromethane. In the second step the resulting ketoesters are hydrolysed. This is a general method. The yields ofmeta-acylphenols are between 40 and 90%. The isomeric 2-acyl-4-methoxy-phenols which were partly unknown or accessible only in low yields have also been prepared for comparative spectral studies (UV, IR, NMR, MS) ofortho- andmeta-acylphenols.
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Literatur
Armstrong, E. C., Bent, R. L., Loria, A., Thirtle, J. R., Weissberger, A., J. Amer. Chem. Soc.82, 1928 (1960).
Cruickshank, J. H., Robinson, R. J. Chem. Soc. (C)1938, 2064.
Amin, G. C., Shah, N. M., J. Indian. Chem. Soc.27, 531 (1950).
Tadkod, R. S., Kulkarni, J. N., Nargund, K. S., J. Karnatak Univ.3, 78 (1958); Chem. Abstr.54, 8717 (1960).
Gore, P. H., in: Friedel-Crafts and Related Reactions (Olah, G. A., Hrsg.), Vol. 3, Part I, p. 51, eq. (100). New York: Wiley Interscience. 1964.
Martin, R., Bull. Soc. chim. France1977, 901.
Böeseken, J., Rec. Trav. chim.29, 100 (1910).
Olah, G. A., Germain, A., White, A. M., in: Carbonium Ions (Olah, G. A., Schleyer, P. v. R., Hrsg.), Vol. 5, S. 2123. New York: Wiley Interscience. 1976.
Cook, A. H., Heilbron, I. M., Lewis, F. B., J. Chem. Soc. (C)1942, 659.
Kauffmann, H., Brombach, A., Ber.38, 794 (1905); Ann. Chem.344, 65 (1906).
König, B., Kostanecki, St. v., Ber.39, 4027 (1906).
Auwers, K. v., Pohl, P., Ann. Chem.405, 281 (1914).
Simonis, H., Danischewski, S., Ber.59, 2914 (1926).
Bogert, M. T., Howells, H. P., J. Amer. Chem. Soc.52, 837 (1930).
Waldmann, H., Ber.83, 171 (1950).
Philbin, E. M., Swirski, J., Wheeler, T. S., Chem. and Ind.1955, 445; J. Chem. Soc. (C)1956, 4455.
Dean, F. M., Goodchild, J., Houghton, L. E., Martin, J. A., Morton, B. B., Parton, B., Price, A. W., Somvichien, Nougyow, Tetrahedron Lett.1966, 4153.
Martin, R., unveröffentlichte Versuche.
Martin, R., Betoux, J.-M., Bull. Soc. chim France1973, 143.
Casadio, S., Pala, G., Crescenzi, R., Marazzi-Uberti, E., Fresia, P., Arzneim-Forsch.16, 592 (1966).
McKillop, A., Curtis, T. E., Deutsches Patent, 1969, 1, 903.
Auwers K. v., Müller, W., Ber.50, (2), 1175 (1917).
Pfeiffer, P. v., Wang, L., Angew. Chem.40, 990 (1927).
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Martin, R. Untersuchungen zurFriedel-Crafts-Reaktion. XVI. Darstellung isomerer 2-Acyl- und 3-Acyl-4-methoxyphenole. Monatshefte für Chemie 112, 1155–1163 (1981). https://doi.org/10.1007/BF00905470
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DOI: https://doi.org/10.1007/BF00905470