The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Apr. 07, 2015

Filed:

Jun. 21, 2012
Applicant:

George A. Kraus, Ames, IA (US);

Inventor:

George A. Kraus, Ames, IA (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07C 67/313 (2006.01); C07C 51/377 (2006.01); C07C 67/317 (2006.01); C07C 67/343 (2006.01); C07C 51/367 (2006.01);
U.S. Cl.
CPC ...
C07C 67/317 (2013.01); C07C 67/313 (2013.01); C07C 67/343 (2013.01); C07C 51/367 (2013.01); C07C 51/377 (2013.01); C07C 2103/66 (2013.01); C07C 2103/86 (2013.01);
Abstract

A method of synthesis of para-substituted benzoate esters and acids is provided, wherein the para-substituted regioisomer is obtained substantially free of the meta-substituted impurity, the method comprising contacting a coumalate ester or acid and an unactivated alkene at elevated temperature in the presence of a metal oxidation catalyst and an oxidant. The metal oxidation catalyst can be palladium, such as palladium on carbon, and the oxidant can be the oxygen gas in ambient air. The reaction can be carried out without solvent or in high boiling hydrocarbon solvents such as mesitylene. When the unactivated alkene is a monosubstituted alkene, yields of at least about 50 or 60% of para-substituted ester and acid products, respectively, are obtained, substantially free of the regioisomeric meta-substituted impurity.


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