Wikipedia

File:HMB synthesis 2.svg

Original file ‎(SVG file, nominally 793 × 389 pixels, file size: 90 KB)

Summary

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

A cycloaddition reaction between acetone and ketene depending on the conditions produce β-isovalerolactone or 4,4-dimethyloxetan-2-one.[1][2] Hydrolysis of either of these lactones under basic conditions yields HMB. HMB can also be prepared through the exhaustive halogenation of the methyl ketone of diacetone alcohol (the haloform reaction) with sodium hypobromite or sodium hypochlorite.[3][4][5] Diacetone alcohol in turn may be prepared through the aldol condensation of acetone. The carboxylation of tert-butyl alcohol with carbon monoxide and Fenton's reagent (hydrogen peroxide and ferrous iron) has also been used to synthesize HMB.[3][6] Alternatively, HMB can be prepared through microbial oxidation of β-methylbutyric acid by the fungus Galactomyces reessii.[7]

References
  1. ↑ (January 1954). "β-Propiolactone. XIV. β-Isovalerolactone". Journal of the American Chemical Society 76 (2): 486–488. DOI:10.1021/ja01631a045.
  2. ↑ WO application 2015094925, White TO, "Stable liquid filled hard capsule comprising beta-hydroxy-beta-methylbutyric acid", published 25 June 2015, assigned to Capsugel Belgium Nv
  3. ↑ a b (June 1958). "Syntheses by Free-radical Reactions. V. A New Synthesis of Carboxylic Acids". Journal of the American Chemical Society 80 (11): 2882–2887. DOI:10.1021/ja01544a072.
  4. ↑ (September 1903). "Zur Kenntnis des Diacetonalkohols und des Mesityloxyds". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften 24 (9): 765–772. DOI:10.1007/BF01526057.
  5. ↑ "Example 5.2" in (February 2001) Organic Synthesis Engineering, Category:New York: Oxford University Press, pp. 102–124 ISBN: 978-0-19-509689-7.
  6. ↑ "Homolytic Mechanism in Metal Catalysis" in (December 2012) Organometallic Mechanisms and Catalysis: The Role of Reactive Intermediates in Organic Processes, Category:New York: Elsevier, p. 67 ISBN: 978-0-323-14410-0.
  7. ↑ (November 1997). "Conversion of beta-methylbutyric acid to beta-hydroxy-beta-methylbutyric acid by Galactomyces reessii". Applied and Environmental Microbiology 63 (11): 4191–4195. PMID 9361403. PMC: 168736.
Date
Source Own work
Author Boghog

Licensing

I, the copyright holder of this work, hereby publish it under the following license:
w:en:Creative Commons
attribution share alike
This file is licensed under the Creative Commons Attribution-Share Alike 4.0 International license.
You are free:
  • to share – to copy, distribute and transmit the work
  • to remix – to adapt the work
Under the following conditions:
  • attribution – You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
  • share alike – If you remix, transform, or build upon the material, you must distribute your contributions under the same or compatible license as the original.

Captions

Add a one-line explanation of what this file represents

Items portrayed in this file

depicts

inception

23 September 2016

File history

Click on a date/time to view the file as it appeared at that time.

Date/TimeThumbnailDimensionsUserComment
current04:00, 3 April 2018Thumbnail for version as of 04:00, 3 April 2018793 × 389 (90 KB)Boghogfixed bond order in carbon monoxide (double → triple) italicized tert in tert-butylanol
19:59, 23 September 2016Thumbnail for version as of 19:59, 23 September 2016793 × 389 (88 KB)BoghogUser created page with UploadWizard
The following pages on the English Wikipedia use this file (pages on other projects are not listed):

Metadata

This file contains additional information, probably added from the digital camera or scanner used to create or digitize it.

If the file has been modified from its original state, some details may not fully reflect the modified file.

Retrieved from "https://en.wikipedia.org/wiki/File:HMB_synthesis_2.svg"