2-Hydroxy-3-[(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy]-4-methoxy-6-propylbenzoic acid methyl ester

Base Information

• Chemical Name: 2-Hydroxy-3-[(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy]-4-methoxy-6-propylbenzoic acid methyl ester
• CAS No.: 6161-77-9
• Molecular Formula: C23H28O8
• Molecular Weight: 432.46
• Mol file: 6161-77-9.mol

Synonyms:2-Hydroxy-3-[(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy]-4-methoxy-6-propylbenzoic acid methyl ester;Sekikaic acid methyl ester

Chemical Property of 2-Hydroxy-3-[(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy]-4-methoxy-6-propylbenzoic acid methyl ester

Chemical Property:

• PSA: 111.52000
• LogP: 4.02580

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Hydroxy-3-[(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy]-4-methoxy-6-propylbenzoic acid methyl ester

There total 13 articles about 2-Hydroxy-3-[(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy]-4-methoxy-6-propylbenzoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

2-hydroxy-4-methoxy-6-propylbenzoic acid (6245-56-3) + methyl 2,3-dihydroxy-4-methoxy-6-propylbenzoate → sekikaic acid methyl ester (6161-77-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 23 ℃; for 14h;

DOI:10.1002/anie.201506232

Reference yield:

methyl 5-hydroxy-4-methoxy-2-propylbenzoate → sekikaic acid methyl ester (6161-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h / 55 °C

2.1: phthaloyl peroxide / 2,2,2-trifluoroethanol / 4 h / 23 °C

2.2: 6 h / 40 °C

3.1: boron trichloride / dichloromethane / 6 h / 23 °C

4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 14 h / 23 °C

With dmap; phthaloyl peroxide; boron trichloride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.201506232

Reference yield:

3-ethoxycyclopent-2-en-1-one (22627-70-9) → sekikaic acid methyl ester (6161-77-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tetrahydrofuran; diethyl ether / 4.5 h / 23 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 16.75 h / -78 - 23 °C

3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 2 h / -78 °C

4.1: magnesium sulfate; silver(l) oxide / 16 h / 23 °C

5.1: sulfolane / 0.33 h / 190 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h / 55 °C

7.1: phthaloyl peroxide / 2,2,2-trifluoroethanol / 4 h / 23 °C

7.2: 6 h / 40 °C

8.1: boron trichloride / dichloromethane / 6 h / 23 °C

9.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 14 h / 23 °C

With dmap; n-butyllithium; phthaloyl peroxide; boron trichloride; magnesium sulfate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; silver(l) oxide; lithium hexamethyldisilazane; In tetrahydrofuran; sulfolane; diethyl ether; hexane; dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.201506232

upstream raw materials:

diazomethane

sekikaic acid

3-ethoxycyclopent-2-en-1-one

2-hydroxy-4-methoxy-6-propylbenzoic acid

Downstream raw materials:

2-hydroxy-4-methoxy-6-propylbenzoic acid

Refernces