33173-34-1Relevant articles and documents
Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
supporting information, p. 6648 - 6653 (2021/09/08)
The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
Claisen condensation as a facile route to an α-alkoxy-cinnamate: Synthesis of ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate
Linderberg, Mats T.,Moge, Mikael,Sivadasan, Sivaprasad
, p. 838 - 845 (2013/09/03)
The title compound was prepared from p-anisaldehyde and ethyl ethoxyacetate via a racemic synthetic route. The synthesis involves a Claisen-type condensation in which the elimination was unexpectedly promoted by an excess of the ester. The process has been successfully performed on a 2000-L scale with a total yield over seven steps of 19%.
Unstable 1,1,2-Enetriols as (Probable) Intermediates in the Decarboxylation of α,β-Diketo Acids
Dahn, Hans,Rotzler, Gerhard
, p. 3080 - 3082 (2007/10/02)
During the acid hydrolysis of (hydrated) 4-aryl-2,3-diketobutyramide 2 (aryl = phenyl, o-chlorophenyl, p-methoxyphenyl), 3-aryllactic acid (5) is formed by rapid decarboxylation of the intermediate diketo acid (3).In the decarboxylation step, a further unstable intermediate is formed.The latter manifests itself by reducing 1 mol of added iodine during the hydrolysis-decarboxylation reaction, thereby forming 3-arylpyruvic acid (6), isolated instead of 5.Thus, the oxidation of the unstable intermediate by iodine is more rapid than its ketonization.It is formulated as an 1,1,2-enetriol (4), more probably than an α-hydroxyketone.