Synthesis of di‐ and polycarboxylic acids and esters

Kucherov, V. F.; Yanovskaya, L. A.

doi:10.1002/9780470771099.ch5

Cited by 2 publications

(1 citation statement)

References 174 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Dicarboxylic acids and their derivatives are important synthetic intermediates in the synthesis of various kinds of polyfunctionalized systems . Among them, unsymmetrical acid derivatives are valuable tools for elaborate molecular design. , While succinic (or adipic) acid amide esters are easily prepared by aminolysis of corresponding acid anhydrides, synthesis of unsymmetrical derivatives of malonic acid cannot be performed in a similar way because malonic anhydride is not commonly used. Hence, they are generally prepared by aminolysis of diethyl malonate or by chemical conversion from malonic acid …”

Section: Introductionmentioning

confidence: 99%

Transacylation of α-Aryl-β-keto Esters

et al. 2003

View full text Add to dashboard Cite

The acyl group of an alpha-aryl-beta-keto ester was readily transferred to N-, O-, and S-nucleophiles. The transacylation from arylated diethyl 3-oxoglutarate to amines led to unsymmetrical malonic acid amide esters in high yields. The present reaction proceeded under mild conditions without formation of detectable byproducts. Only simple experimental manipulations were required. This reaction was also found to be sensitive to steric factors, which enabled the chemoselective monoacylation of diamines and amino alcohols without any modifications such as protection.

show abstract

Section: Introductionmentioning

confidence: 99%

Transacylation of α-Aryl-β-keto Esters

et al. 2003

View full text Add to dashboard Cite

show abstract

Fat‐based dibasic acids

Kadesch¹

1979

J Americ Oil Chem Soc

View full text Add to dashboard Cite

Aside from “dimer acids” (E.C. Leonard's paper), the best known fat‐based dibasic acids consist of eight product types of which only four are commercially important. These are described in detail in this paper: (a.) Azelaic acid produced from oleic acid by either chrome oxidation or ozonolysis of oleic acid also, “brassylic” acid from mixed 55% erucic‐containing crambe oil fatty acids. (b). Sebacic acid from castor oil or possibly dodecanedioic acid from lesquerolic acid by caustic fusion. (c) C‐21 Dibasic acid by Diels Alder reaction between isomerized TOFA and acrylic acid. (d.) C‐19 Dibasic acids (carboxystearic acids) from oleic acid by carboxylation. (e.) Mixed C‐11/C‐12 Dibasic acids by several routes. Both the alkali cleavage and gentle nitric acid oxidations of certain hydroxy fatty acids (e.g., 12‐hydroxystearic acid from hydrogenation of ricinoleic acid, etc.) can be used to afford mixed C‐11/C‐12 dibasic acids. (f.) Dibasic acid mixtures by nitric acid oxidations. Depending upon conditions, both saturated and unsaturated fatty acids are oxidized to a heterogeneous mixture of mono‐ and dibasic acids by oxidation with nitric acid.

show abstract

Synthesis of di‐ and polycarboxylic acids and esters

Cited by 2 publications

References 174 publications

Transacylation of α-Aryl-β-keto Esters

Transacylation of α-Aryl-β-keto Esters

Fat‐based dibasic acids

Contact Info

Product

Resources

About