Abstract
8-(4-n-Hexylcyclohex-2-enyl)octanoic acid obtained by the addition of ethylene totrans,trans-9,11-octadecadienoic acid was treated with 28% hydrogen peroxide in acetic or formic acid to give the hydroxyacetoxy or-formoxy derivative. Saponification of the hydroxyacetoxy derivative yielded two crystalline glycols. The hydroxyformoxy fatty acid was converted in one step either to the glycol ester, methyl 8-(4-n-hexyl-2,3-dihydroxycyclohexyl)octanoate, by reaction with anhydrous hydrochloric acid in methanol or to the acetone derivative of the glycol ester by treatment with dimethoxypropane and anhydrous hydrochloric acid in methanol. Epoxidation of the C20 cyclohexene fatty methyl ester gave the oxirane derivative. A ring opening reaction of the diol acid with periodic acid yielded 9,12-diformylstearic acid.
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References
Danzig, M. J., J. L. O’Donnell, E. W. Bell, J. C. Cowan and H. M. Teeter, JAOCS34, 136–138 (1957).
Gast, L. E., E. W. Bell and H. M. Teeter, Ibid.33, 278–281 (1956).
Teeter, H. M., E. W. Bell, J. L. O’Donnell, M. J. Danzig and J. C. Cowan, Ibid.35, 238–240 (1958).
Teeter, H. M., J. L. O’Donnell, W. J. Schneider, L. E. Gast and M. J. Danzig, J. Org. Chem.22, 512–514 (1957).
Friedrich, J. P., E. W. Bell and R. E. Beal, JAOCS39, 420 (1962).
Friedrich, J. P., D. Hejeebu, L. E. Gast and J. C. Cowan, Presented at the 58th AOCS Meeting, New Orleans, La. May, 1967, Abstract No. 126.
Kaufmann, H. P., Fette Seifen Anstrichmittel64, 1115–1126 (1962).
Adams, R., and T. G. Geissmann, J. Am. Chem. Soc.61, 2083–2089 (1939).
Holmes, H. L., Org. Reactions4, 60–173 (1948).
Kloetzel, M. C., Ibid.4, 1–59 (1948).
Martin, J. G., and R. K. Hill, Chem. Rev.61, 537–562 (1961).
Gould, E. S. “Mechanism and Structure in Organic Chemistry,” Holt, Rinehart and Winston, New York, 1959, p. 534.
Hanack, M., “Conformation Theory,” Academic Press, New York, 1965, p. 147.
Richborn, B., and S. Y. Luo, J. Org. Chem.30, 2212–2216 (1965).
Freedman, B., JAOCS44, 113–116 (1967).
Wood, R. D., P. K. Raju and R. Reiser, Ibid.42, 81–85 (1965).
Durbetaki, A. J., Anal. Chem.28, 2000 (1956).
O’Donnell, J. L., L. E. Gast, J. C. Cowan, W. J. DeJarlais and G. E. McManis, JAOCS44, 652–655 (1967).
Kuester, F. E., U.S. Patent 3,127,418 (1964).
Handschumaker, E., and L. Linters, JAOCS24, 143–145 (1947).
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No. Utiliz. Res. Dev. Div., ARS, USDA.
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Dufek, E.J., Gast, L.E. & Friedrich, J.P. Ethylene adduct of conjugated octadecadienoic acids: I. Peracid oxidation products. J Am Oil Chem Soc 47, 47–50 (1970). https://doi.org/10.1007/BF02541456
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DOI: https://doi.org/10.1007/BF02541456