Helvetica Chimica Acta p. 1320 - 1325 (1987)
Update date:2022-08-11
Topics:
Griesbeck, Axel
Seebach, Dieter
Condensation of (R)-3-hydroxybutanoic acid (1) with ethyl orthoacetate gives a 2-ethoxy-substituted 1,3-dioxanone 2 which is thermally labile: at ca. 100 deg C, two competing processes commence, one leading to ethyl (R)-3-acetoxybutanoate (3), the other one - with complete inversion of configuration - to the (S)-4-methyloxetan-2-one (4) and ethyl acetate.These can be readily separated by fractional distillation.Thus, enantiomerically pure (S)-3-hydroxybutanoic acid (ent-1) and l-2-alkyl-3-hydroxybutanoic acid derivatives (such as 6 and 8) become available from the biopolymer PHB, the precursor to the acid 1.
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