Application of ion-exclusion and ion-exchange techniques in preparing 2,3-dihydroxy-2-methylbutanamide and 2,3-dihydroxy-2-methylbutanoic acid from acetoin via the cyanohydrin synthesis

✍ Scribed by J.E. Powell; S. Kulprathipanja; D.A. Johnson; H.R. Burkholder

• Publisher: Elsevier Science
• Year: 1972
• Tongue: English
• Weight: 387 KB
• Volume: 74
• Category: Article
• ISSN: 1873-3778
• DOI: 10.1016/s0021-9673(01)86155-0

✦ Synopsis

The techniques of ion exclusion and ion exchange have been exploited to obtain substantial yields of 2,3-dihydroxy-z-methylbutanamide and z,S-dihydroxy-zmethylbutanoic acid, respectively, following acid hydrolysis of acetoin cyanohydtin. The reaction of acetoin with anhydrous HCN appears to be stereospecific, since the overall process yields an unexpectedly high percentage of only one of two possible diastereomeric &-acid mixtures, namely, the racemate comprised of (2S,3R)-2,3dihydroxy-2-methylbutanoic and (zR,zS)-2,3-dihydroxy-z-methylbutanoic acids.