4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-[4-(acetyloxy)phenyl]-6-(3-methyl-2-butenyl)-

Base Information

• Chemical Name: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-[4-(acetyloxy)phenyl]-6-(3-methyl-2-butenyl)-
• CAS No.: 51225-29-7
• Molecular Formula: C26H24O8
• Molecular Weight: 464.472
• Mol file: 51225-29-7.mol

Synonyms:

Chemical Property of 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-[4-(acetyloxy)phenyl]-6-(3-methyl-2-butenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-[4-(acetyloxy)phenyl]-6-(3-methyl-2-butenyl)-

There total 20 articles about 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-[4-(acetyloxy)phenyl]-6-(3-methyl-2-butenyl)- 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: 71.0%

erythrinin B (51225-30-0) + acetic anhydride (108-24-7) → 5,7,4'-triacetoxy-6-(3-methyl-2-butenyl)isoflavone (51225-29-7)

Guidance literature:

With pyridine; at 115 ℃; for 2h;

DOI:10.1016/j.tet.2006.06.066

Reference yield:

2',4'-dihydroxy-3'-iodo-6'-(methoxymethoxy)acetophenone (321569-79-3) → 5,7,4'-triacetoxy-6-(3-methyl-2-butenyl)isoflavone (51225-29-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 82 percent / potassium carbonate / dimethylformamide / 1 h / 70 °C

2: potassium hydroxide / ethanol / 1 h / Heating

3: 5.48 g / aq. HCl / ethanol; CHCl₃ / 1 h / 40 °C

4: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C

5: [hydroxy(tosyloxy)iodo]benzene / CHCl₃ / 24 h / 20 °C

6: 3.82 g / aq. sodium hydroxide; methanol / CHCl₃ / 5 h / 25 °C

7: 91 percent / triethylamine; PPh₃; CuI / PdCl₂ / dimethylformamide / 2 h / 80 °C

8: 88 percent / hydrogen / palladium on carbon / methanol; dioxane

9: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C

10: 84 percent / potassium carbonate / acetone / 2 h / Heating

11: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating

12: 91 percent / BCl₃ / CH₂Cl₂ / 2.5 h / 20 - 25 °C

13: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C

14: 71 percent / pyridine / 2 h / 110 °C

With pyridine; hydrogenchloride; methanol; potassium hydroxide; sodium hydroxide; copper(l) iodide; [hydroxy(tosyloxy)iodo]benzene; hydrogen; boron trichloride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; palladium dichloride; In 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1080/00397910500514121

Reference yield:

2',4'-bis(benzyloxy)-3'-iodo-6'-(methoxymethoxy)acetophenone (321569-81-7) → 5,7,4'-triacetoxy-6-(3-methyl-2-butenyl)isoflavone (51225-29-7)

Guidance literature:

Multi-step reaction with 13 steps

1: potassium hydroxide / ethanol / 1 h / Heating

2: 5.48 g / aq. HCl / ethanol; CHCl₃ / 1 h / 40 °C

3: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C

4: [hydroxy(tosyloxy)iodo]benzene / CHCl₃ / 24 h / 20 °C

5: 3.82 g / aq. sodium hydroxide; methanol / CHCl₃ / 5 h / 25 °C

6: 91 percent / triethylamine; PPh₃; CuI / PdCl₂ / dimethylformamide / 2 h / 80 °C

7: 88 percent / hydrogen / palladium on carbon / methanol; dioxane

8: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C

9: 84 percent / potassium carbonate / acetone / 2 h / Heating

10: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating

11: 91 percent / BCl₃ / CH₂Cl₂ / 2.5 h / 20 - 25 °C

12: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C

13: 71 percent / pyridine / 2 h / 110 °C

With pyridine; hydrogenchloride; methanol; potassium hydroxide; sodium hydroxide; copper(l) iodide; [hydroxy(tosyloxy)iodo]benzene; hydrogen; boron trichloride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; palladium dichloride; In 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1080/00397910500514121

upstream raw materials:

erythrinin B

acetic anhydride

2',4'-dihydroxy-3'-iodo-6'-(methoxymethoxy)acetophenone

2',4'-bis(benzyloxy)-3'-iodo-6'-(methoxymethoxy)acetophenone