Hydroxytyrosol dihydrocaffeate having antioxidant activity and a method for preparing the same

Patent metadata

Field	Value
Publication number	US-10640450-B1
Application number	US-201916724206-A
Country	US
Kind code	B1
Filing date	Dec 21, 2019
Priority date	Dec 11, 2019
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

A compound having the formula (I):

is disclosed. A method of preparing the compound of formula (I) is also disclosed.

First claim

What is claimed is:

1. A method of preparing a compound having the following formula (I):

comprising:
reacting a compound of formula (II) with a compound of formula (III) in an organic solvent to obtain the compound of formula (I):

2. The method of claim 1 , wherein the reaction of the compound of formula (II) with the compound of formula (III) comprises the following steps:
placing the compound of formula (II), a catalyst, and an organic solvent in a reactor under nitrogen atmosphere, the catalyst being EDC;
adding the compound of formula (III) to the reactor to form a reaction mixture;
heating the reaction mixture at 50-85° C. for 1-4 hours;
concentrated the reaction mixture to obtain a crude product; and
purifying the crude product by a silica gel column, eluting with an ethyl acetate/petroleum ether solvent as an eluent, to obtain the compound of formula (I).

3. The method of claim 2 , wherein the organic solvent is toluene, ethyl acetate, or acetonitrile.

4. The method of claim 2 , wherein the compound of formula (II) and the compound (III) have a molar ratio of 1:1 to 1:1.3.

5. The method of claim 4 , wherein the molar ratio is 1:1.1.

6. The method of claim 2 , wherein the reaction mixture is heated at 75° C. for 4 hours.

7. The method of claim 2 , wherein the ethyl acetate/petroleum ether solvent has a ethyl acetate:petroleum volume ratio of 3:10.

8. The method of claim 1 , wherein the reaction of the compound of formula (II) with the compound of formula (III) comprises the following steps:
placing the compound of formula (II), a catalyst, and an ionic liquid in a reactor under nitrogen atmosphere, the catalyst being 12-molybdosilicic acid hydrate (H 6 Mo 12 O 41 Si);
adding the compound of formula (III) to the reactor to form a reaction mixture;
heating the reaction mixture at 25-50° C. for 5-10 hours;
placing the reaction mixture in a separating funnel to separate a crude product; and
purifying the crude product by recrystallization in methanol to obtain the compound of formula (I).

9. The method of claim 8 , wherein the ionic liquid is 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF 4 ]).

10. The method of claim 8 , wherein the compound of formula (II) and the compound (III) have a molar ratio of 1:1 to 1:1.3.

11. The method of claim 10 , wherein the molar ratio is 1:1.1.

12. The method of claim 8 , wherein the reaction mixture is heated at 25° C. for 8 hours.

Assignees

• Tian Bin
• Ju Xingke
• Li Jingyi
• Xin Liang
• Li Han
• Qi Liang
• Zhao Qianqian
• Wang Yongbo
• Yang Dan
• Liang Chengyuan
• Yao Wenbo
• Univ Shaanxi Science & Tech

Inventors

• Tian Bin
• Ju Xingke
• Li Jingyi
• Xin Liang
• Li Han
• Qi Liang
• Zhao Qianqian
• Wang Yongbo
• Yang Dan
• Liang Chengyuan
• Yao Wenbo

Classifications

• B01J31/0247

  Imides, amides or imidates (R-C=NR(OR)) · CPC title

• C07C69/675 Primary

  of saturated hydroxy-carboxylic acids · CPC title

• C07C67/56

  by solid-liquid treatment; by chemisorption · CPC title

• C07C67/08 Primary

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

• C07C67/52

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