Abstract
IN the course of work on the microbial metabolism of glycine and glyoxylic acid we have had occasion to isolate formic acid as the p-bromophenacyl ester which is widely quoted1,2 as having m.p. 140°. It was observed that the derivative, m.p. 140–42°, isolated from authentic sodium 14C-formate (95,200 counts/min./µmol.) was inactive and showed no depression in melting point when mixed with p-bromophenacyl alcohol, m.p. 142°. A search of the literature revealed that Neish and Lemieux3 have made a similar observation and have described a preparation of authentic p-bromophenacylformate, m.p. 92°. In my hands the methods of Neish and Lemieux yields a derivative, m.p. 98° (92,200 counts/min./µmol.), when the above-labelled formate is used in the preparation (cf. Heilbron and Bunbury4, who quote m.p. 99°).
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References
Hurd, C. D., and Christ, R. E., J. Amer. Chem. Soc., 57, 2007 (1935).
Vogel, A. I., Textbook of Practical Organic Chemistry, third ed. (Longmans, Green and Co., London, 1956).
Neish, A. C., and Lemieux, R. U., Canad. J. Res., 30, 454 (1952).
Heilbron, I., and Bunbury, H. M., Dictionary of Organic Compounds (Eyre and Spottiswoode, London, 1953).
Campbell, L. L., J. Bact., 68, 598 (1954).
Campbell, L. L., J. Biol. Chem., 217, 669 (1955).
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CROSBIE, G. Identification of Formic Acid as the p-Bromophenacyl Ester. Nature 193, 579 (1962). https://doi.org/10.1038/193579a0
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DOI: https://doi.org/10.1038/193579a0
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