Reduktion mehrbasischer α‐Oxy‐säuren bei kombinierter Einwirkung von Katalysatoren

Ipatiew, W.; Rasuwajew, G.

doi:10.1002/cber.19270600850

Cited by 1 publication

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It has been proposed that all these processes are basically similar and proceed through the intermediate formation of pyruvic acid, and then of a ketovalero- Another special method for the preparation of methylsuccinic acid in good yield calls for the action of hydrogen under pressure on solutions of sodium lactate (334).…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

Syntheses Of Alkylated Alkanedioic Acids

Diaper¹,

KUKSIS²

1959

Chem. Rev.

View full text Add to dashboard Cite

example of such a synthesis is the conversion of 2-pentenal, through a Reformatsky condensation with ethyl -bromopropionate and oxalation of the unsaturated product, eventually to 2,6-dimethylsuberic acid (401).It has been shown that formates and oxalates may function as carbonyl components in a Reformatsky synthesis. Ethyl -bromoisobutyrate reacts with ethyl oxalate (569) and with ethyl formate (82), giving hydroxy esters which could be converted to 2,2-dimethylsuccinic and 2,2,4,4-tetramethyIglutaric acids, respectively.The application of the Reformatsky reaction to nitriles (154) leads to the formation of ketones in a manner comparable with the Grignard reaction and is a convenient method for the synthesis of /3-keto esters.By varying the nature of the carbonyl compounds and the halo esters employed, many alkylated dicarboxylic acids have been prepared with the help of this reaction, yet the possible products may be of only a few types. Branching is confined to the a-and ß-positions at one or both ends of the chain, and while the -position may bear one, two, or no alkyl groups, the /3-position cannot bear more than one side chain.Theoretically, in all of the above cases the ester groups of the final products may be converted into aldehyde or keto groups through the acyl chlorides and dialkyl metals (142).A repetition of the Reformatsky process would lengthen the chain with or without further branching at the new points of junction of carbon chains (629).

show abstract

Section: Miscellaneous Methodsmentioning

confidence: 99%