Production of malonic anhydrides and derivatives thereof
AssigneeThe Regents of the University of California
InventorCharles L. Perrin
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Abstract
Malonic anhydride and substituted malonic anhydrides are prepared by ozonolysis of the enol-lactone dimers of ketenes. The resulting malonic anhydrides can be hydrolyzed with water to form the corresponding acid, reacted with an alcohol to yield the monoester, or reacted with an amine to yield the monoamide.
Claims10
A process for producing a derivative of a malonic anhydride selected from the group consisting of a malonic acid, a malonic acid monoester and a malonic acid monoamide, which comprises passing ozone through an inert organic solvent containing an enol-lactone dimer of a ketene, said dimer of a ketene having the general formula ##STR3## where R and R' are selected from the group consisting of hydrogen, alkyl having a chain length ranging from C.sub.1 to C.sub.20, cycloalkyl containing from about 3 to about 8 carbon atoms, carbocyclic aryl, said aryl groups containing from about 6 to about 20 carbon atoms, and where R and R' can be the same or different, and where R and R' together can constitute the atoms necessary to form a carbocyclic ring of from about 4 to about 8 carbon atoms, said solvent being maintained at a temperature ranging from about -100.degree. C. to about 0.degree. C., and forming a malonic anhydride having the formula ##STR4## where R and R' are defined as above, adding a derivatizing agent selected from the group consisting of water, alcohols, phenols, ammonia and amines to the reaction mixture, and permitting the reaction mixture to warm to about room temperature.
A process for producing a derivative of a malonic anhydride selected from the group consisting of a malonic acid monoester and a malonic acid monoamide, which comprises subjecting an enol-lactone dimer of a ketene to ozonolysis in an inert solvent, and forming a malonic anhydride, said enol-lactone dimer of a ketene having the general formula:
- ##STR6## where R and R' are selected from the group consisting of hydrogen, alkyl, cycloalkyl, carbocyclic aryl, and where R and R' can be the same or different, and where R and R' together can constitute the atoms necessary to form a carbocyclic ring, adding a derivatizing agent to the solution, said derivatizing agent being selected from the group consisting of alcohols, phenols, ammonia and amines, and forming the corresponding malonic acid monoester or malonic acid monoamide derivative of said malonic anhydride.
Dependencies are inferred from the claim text.