Pyrogallol[2]resorcin[2]arene

Patent metadata

Field	Value
Publication number	US-11629113-B2
Application number	US-202117515891-A
Country	US
Kind code	B2
Filing date	Nov 1, 2021
Priority date	Oct 30, 2020
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

A one pot synthesis of a mixed macrocycle of resorcinol and pyrogallol is disclosed using an acidic catalyst by conventional as well as by microwave assisted methods. Compared with traditional synthesis, the microwave mediated tactic provides a simple, greener route and affords higher compound yields in a shorter period. Moreover, the catalyst can be efficiently reused without any loss in activity.

First claim

What is claimed is:

1. A composition comprising pyrogallol[2]resorcin[2]arene.

2. A method of making a mixed macrocycle of resorcinol and pyrogallol comprising:
a. mixing pyrogallol and resorcinol with an aldehyde in a solvent selected from the group consisting of acetonitrile, ethanol, acetone, water and combinations thereof;
b. irradiating the mixture using microwaves to produce a product; and
c. crystallizing the product;
wherein the product comprises the mixed macrocycle.

3. The method of claim 2 wherein the mixture is irradiated in the presence of at least one catalyst selected from the group consisting of concentrated HCl, a macroreticular polystyrene-based sulfonic acid ion exchange resin and sulfonated graphitic carbon nitride.

4. The method of claim 3 wherein the catalyst is a macroreticular polystyrene-based sulfonic acid ion exchange resin.

5. The method of claim 3 wherein the catalyst is sulfonated graphitic carbon nitride.

6. The method of claim 2 wherein the aldehyde is one carbon higher than the required alkyl length.

7. The method of claim 2 wherein the solvent is acetonitrile.

8. The method of claim 2 wherein the mixture is irradiated at a temperature of at least 70° C.

9. The method of claim 2 wherein the mixture is irradiated at a temperature of at least 80° C.

10. The method of claim 8 wherein the mixture is irradiated for at least 10 minutes.

11. The method of claim 8 wherein the mixture is irradiated for at least 15 minutes.

12. A method of making a mixed macrocycle of resorcinol and pyrogallol comprising:
a. mixing pyrogallol and resorcinol with an aldehyde in a solvent selected from the group consisting of acetonitrile, ethanol, acetone, water and combinations thereof;
b. heating the mixture in the presence of at least one catalyst selected from the group consisting of concentrated HCl, a macroreticular polystyrene-based sulfonic acid ion exchange resin and sulfonated graphitic carbon nitride, to produce a product; and
c. crystallizing the product;
wherein the product comprises the mixed macrocycle.

13. The method of claim 12 wherein the catalyst is a macroreticular polystyrene-based sulfonic acid ion exchange resin.

14. The method of claim 12 wherein the catalyst is sulfonated graphitic carbon nitride.

15. The method of claim 12 wherein the aldehyde is one carbon higher than the required alkyl length.

16. The method of claim 12 wherein the solvent is acetonitrile.

Assignees

• Univ Cincinnati

Inventors

• Kumari Harshita

Classifications

• C07C37/84

  by crystallisation · CPC title

• C07C37/20 Primary

  using aldehydes or ketones · CPC title

• C07C39/17 Primary

  containing other rings in addition to the six-membered aromatic rings {, e.g. cyclohexylphenol} · CPC title

• C07C2603/52

  containing five condensed rings · CPC title

• C07C2521/18

  Carbon · CPC title