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

Base Information

• Chemical Name: 5,7-Bis(acetyloxy)-3-[2,4-bis(acetyloxy)-3-(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one
• CAS No.: 66056-27-7
• Molecular Formula: C₂₈H₂₆O₁₀
• Molecular Weight: 522.508
• Mol file: 66056-27-7.mol

Synonyms:Licoisoflavon A-tetraacetat;Acetic acid 3-acetoxy-6-(5,7-diacetoxy-4-oxo-4H-chromen-3-yl)-2-(3-methyl-but-2-enyl)-phenyl ester;

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

Chemical Property:

• Melting Point: 149 - 150 °C (ethanol)
• PSA: 135.41000
• LogP: 4.66990

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 5,7-Bis(acetyloxy)-3-[2,4-bis(acetyloxy)-3-(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one 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:

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone (18065-05-9) → 2',4',5,7-tetraacetoxy-3'-(3-methyl-2-butenyl)isoflavone (66056-27-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 68 percent / piperidine / ethanol / 6 h / Heating

2: sodium acetate;

3: 79 percent / 1) thallium (III)nitrate trihydrate; 2) 10percent hydrochloric acid; / methanol / 1) 32-35 deg C; 8 h; 2) reflux; 3 h;

4: 97 percent / hydrogenolyse / 10percent Pd-C / methanol

5: 37 percent / pyridine / diethyl ether / 5.5 h / 2 - 5 °C

6: 18 percent / BF₃-etherate / dioxane / 6 h / 51 - 53 °C

7: 50 percent / 4percent aq. NaOH / methanol / 1.5 h / 50 °C

8: sodium acetate

With piperidine; pyridine; hydrogenchloride; sodium hydroxide; hydrogenolyse; boron trifluoride diethyl etherate; sodium acetate; thallium(III) nitrate; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether; ethanol;

DOI:10.1246/bcsj.58.136

Reference yield:

2,4,4',6'-tetrakis(benzyloxy)-2'-hydroxychalcone (82448-60-0) → 2',4',5,7-tetraacetoxy-3'-(3-methyl-2-butenyl)isoflavone (66056-27-7)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium acetate;

2: 79 percent / 1) thallium (III)nitrate trihydrate; 2) 10percent hydrochloric acid; / methanol / 1) 32-35 deg C; 8 h; 2) reflux; 3 h;

3: 97 percent / hydrogenolyse / 10percent Pd-C / methanol

4: 37 percent / pyridine / diethyl ether / 5.5 h / 2 - 5 °C

5: 18 percent / BF₃-etherate / dioxane / 6 h / 51 - 53 °C

6: 50 percent / 4percent aq. NaOH / methanol / 1.5 h / 50 °C

7: sodium acetate

With pyridine; hydrogenchloride; sodium hydroxide; hydrogenolyse; boron trifluoride diethyl etherate; sodium acetate; thallium(III) nitrate; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether;

DOI:10.1246/bcsj.58.136

Reference yield:

2',4',5,7-tetrakis(benzyloxy)isoflavone (82458-45-5) → 2',4',5,7-tetraacetoxy-3'-(3-methyl-2-butenyl)isoflavone (66056-27-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / hydrogenolyse / 10percent Pd-C / methanol

2: 37 percent / pyridine / diethyl ether / 5.5 h / 2 - 5 °C

3: 18 percent / BF₃-etherate / dioxane / 6 h / 51 - 53 °C

4: 50 percent / 4percent aq. NaOH / methanol / 1.5 h / 50 °C

5: sodium acetate

With pyridine; sodium hydroxide; hydrogenolyse; boron trifluoride diethyl etherate; sodium acetate; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether;

DOI:10.1246/bcsj.58.136

upstream raw materials:

2-methyl-3-buten-2-ol

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

2',4',5,7-tetrahydroxyisoflavone

7-benzoyloxy-2',4',5-trihydroxyisoflavone