A New Synthesis of some Derivatives of 4,4′-Stilbenediol


SYNTHESES of α-alkyl- or α,α′-dialkyl-4,4′-stilbenediols and of their derivatives, several of which exhibit remarkable œstrogenic activity, have so far mostly been by demethylation of the corresponding dimethyl ethers, and have invariably involved several stages1,2. A direct synthesis in one step, of trans-α-methyl-4,4′-stilbenediol (and some of its dialkyl ethers) from phenol (or its corresponding ether) and chloroacetone, has now been accomplished.

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  1. 1

    See, inter alia, Dodds, E. C., Golberg, L., Lawson, W., and Robinson, R., Nature, 141, 247 (1938). Kuwada, S., and Sasagawa, Y., J. Pharm. Soc. Japan, 60, 93 (1940). Kuwada, S., Sasagawa, Y., and Nisikawa, M., ibid., 60, 553 (1940). Vargha, L. v., and Kovács, E., Ber., 75, B, 794 (1942). Kharasch, M. S., and Kleiman, M., J. Amer. Chem. Soc., 65, 11 (1943). Wilds, A. L., and Bigger-staff, W. R., ibid., 67, 789 (1945). Shishido, K., and Nozaki, H., ibid., 70, 776 (1948).

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  2. 2

    Dodds, E. C., Golberg, L., Grünfeld, E. I., Lawson, W., Saffer, C. M., jun., and Robinson, R., Proc. Roy. Soc., B, 132, 83 (1944).

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BHARGAVA, P., ZAHEER, S. A New Synthesis of some Derivatives of 4,4′-Stilbenediol. Nature 171, 746–747 (1953). https://doi.org/10.1038/171746b0

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