Method for the synthesis and purification of aryl acid esters

Patent metadata

Field	Value
Publication number	US-10968162-B2
Application number	US-201916369583-A
Country	US
Kind code	B2
Filing date	Mar 29, 2019
Priority date	Mar 30, 2018
Publication date	Apr 6, 2021
Grant date	Apr 6, 2021

Abstract

The general inventive concepts are directed to the discovery that certain aryl acids can be esterified under particular conditions to provide the resulting ester as a solid that precipitates in good yield from the reaction mixture. The esters may then be isolated and purified with relative ease. Accordingly, a method for the esterification, isolation, and purification of aryl acids is provided.

First claim

The invention claimed is:

1. A method for the synthesis of an aryl ester of formula II,

wherein R 1 , R 2 , R 3 , R 4 , and R 5 each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, a halogen atom, an alkoxy group having from 1 to 6 carbon atoms, a haloalkyl group having from 1 to 6 carbon atoms, a haloalkoxy group having from 1 to 6 carbon atoms, an alkylthio group having from 1 to 6 carbon atoms, an alkylsulphonyl group having from 1 to 6 carbon atoms, a nitro group, a hydroxy group, a cyano group, an amino group, an alkylamino group having from 1 to 6 carbon atoms or a dialkylamino group having from 1 to 6 carbon atoms in each alkyl part,
wherein n is equal to 0 or to an alkyl group having from 1 to 6 carbon atoms,
wherein R 6 represents an alkyl group having from 1 to 6 carbon atoms or a cycloalkyl group having from 3 to 6 carbon atoms,
the method comprises:
mixing an aryl acid according to formula I, with an alcohol solvent and an acid catalyst to form a reaction mixture,

heating the reaction mixture for a period of 0.5 to 10 hours,
filtering the reaction mixture to obtain an aryl ester,
and washing the aryl ester with a second solvent,
wherein the molar ratio of aryl acid to alcohol solvent is 1:100 to 1:5, and wherein the molar ratio of aryl acid:acid catalyst is from 1:0.5 to 1:0.01.

2. The method of claim 1 , wherein the reaction is heated for a period of 0.5 to 6 hours.

3. The method of claim 1 , wherein the molar ratio of aryl acid to alcohol is 1:60 to 1:5.

4. The method of claim 1 , wherein the molar ratio of aryl acid to alcohol is 1:50 to 1:5.

5. The method of claim 1 , wherein the molar ratio of aryl acid to alcohol is 1:20 to 1:5.

6. The method of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, a halogen atom, or an alkoxy group having from 1 to 6 carbon atoms.

7. The method of claim 1 , wherein n is alkyl group having from 1 to 6 carbon atoms.

8. The method of claim 1 , wherein R 6 represents an alkyl group having from 1 to 6 carbon atoms.

9. The method of claim 1 , wherein the second solvent is selected from water, methanol, ethanol, and mixtures thereof.

10. The method of claim 1 , wherein the mixture is cooled prior to filtering.

11. The method of claim 1 , wherein the catalyst is a strong acid.

Assignees

• Univ Miami

Inventors

• Marshall Janet

Classifications

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C201/12

  by reactions not involving the formation of nitro groups · CPC title

• C07C67/52

  by change in the physical state, e.g. crystallisation · CPC title

• C07C67/58 Primary

  by liquid-liquid treatment · CPC title