File:HMB synthesis historical.svg

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Summary

Description
English: Synthetic routes to β-hydroxy β-methylbutyric acid.

The first reported chemical syntheses of HMB were: the oxidation of 2-methylpent-4-en-2-ol with chromic acid (H2CrO4) in 1877 by the Russian chemists Michael and Alexander Zaytsev;[1] the oxidative cleavage of 4-methylpentane-1,2,4-triol with potassium permanganate (KMnO4) in 1880 and 1889 by Schirokoff and Reformatsky, respectively;[2][3] and, the oxidation with permanganate of 3-methylbutane-1,3-diol in 1892 by Kondakow.[4]

References
  1. ↑ The earliest citation for the synthesis of β-hydroxy β-methylbutyric acid in the Reaxys chemical database as of September 2016 is:
    (in german) (1877). "Synthese des Allyldimethylcarbinols". Justus Liebig's Annalen der Chemie 185 (2–3): 151–169. DOI:10.1002/jlac.18771850204.
  2. ↑ (in german) (January 1881). "Ueber die β-Dipropyl- und β-Diäthyläthylenmilchsäure und über die Oxydation des Allyldimethylcarbinols und Diallylcarbinols mit übermangansaurem Kalium". Journal für Praktische Chemie 23 (1): 196–208. DOI:10.1002/prac.18810230115.
  3. ↑ (in german) (30 October 1889). "Synthese einiger Glycerine mittelst unterchloriger Säure". Journal für Praktische Chemie 40 (1): 396–419. DOI:10.1002/prac.18890400137.
  4. ↑ (in russian) (1892). "On the action of mineral acids on dimethylallyls". Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (Journal of the Russian Physico-Chemical Society) 1: 508–513. abstracted by (in german) Grosset (1893). "Ueber die Einwirkung von Mineralsauren auk Dimethylallen". Berichte der Deutschen Chemischen Gesellschaft 26 (4): 96. DOI:10.1002/cber.18930260412.
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6 November 2016

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Date/TimeThumbnailDimensionsUserComment
current05:48, 27 March 2018Thumbnail for version as of 05:48, 27 March 2018609 × 208 (48 KB)wikimediacommons>DMacksmore standard to write chromic acid as "H2CrO4" than "CrO4H2"

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