3-(4-Hydroxyphenyl)-4,7-diphenyl-5-hydroxybenzofuran-2,6-dione

Base Information

• Chemical Name: 3-(4-Hydroxyphenyl)-4,7-diphenyl-5-hydroxybenzofuran-2,6-dione
• CAS No.: 7611-34-9
• Molecular Formula: C₂₆H₁₆O₅
• Molecular Weight: 408.41
• Mol file: 7611-34-9.mol

Synonyms:Xylerythrin;5-Hydroxy-3-(4-hydroxy-phenyl)-4,7-diphenyl-benzofuran-2,6-dione;

Chemical Property of 3-(4-Hydroxyphenyl)-4,7-diphenyl-5-hydroxybenzofuran-2,6-dione

Chemical Property:

• PSA: 83.83000
• LogP: 4.66590

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(4-Hydroxyphenyl)-4,7-diphenyl-5-hydroxybenzofuran-2,6-dione

There total 11 articles about 3-(4-Hydroxyphenyl)-4,7-diphenyl-5-hydroxybenzofuran-2,6-dione 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:

3-hydroxy-1,4-diphenyl-2-butanone (6838-54-6) → xylerythrin (7611-34-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C

2: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C

3: 82 percent / diethyl ether / 0.25 h / 0 °C

4: 90 percent / bromine / acetic acid / 3 h / Ambient temperature

5: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene

6: 92 percent / boron tribromide / hexane; CH₂Cl₂ / 0.5 h / Heating

7: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature

8: 1) acetic anhydride, sodium acetate, 2) 48percent aq. hydrogen bromide / 1) reflux, 3 h, 2) acetic acid, reflux, 0.5 h

With hydrogen bromide; bromine; sodium ethanolate; sodium acetate; acetic anhydride; boron tribromide; triethylamine; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene;

Reference yield:

α-<(trimethylsilyl)oxy>benzenepropanenitrile (93554-96-2) → xylerythrin (7611-34-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 2) dil. aq. hydrochloric acid / 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight

2: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C

3: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C

4: 82 percent / diethyl ether / 0.25 h / 0 °C

5: 90 percent / bromine / acetic acid / 3 h / Ambient temperature

6: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene

7: 92 percent / boron tribromide / hexane; CH₂Cl₂ / 0.5 h / Heating

8: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature

9: 1) acetic anhydride, sodium acetate, 2) 48percent aq. hydrogen bromide / 1) reflux, 3 h, 2) acetic acid, reflux, 0.5 h

With hydrogenchloride; hydrogen bromide; bromine; sodium ethanolate; sodium acetate; acetic anhydride; boron tribromide; triethylamine; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene;

Reference yield:

3-hydroxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione (131146-41-3) → xylerythrin (7611-34-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / diethyl ether / 0.25 h / 0 °C

2: 90 percent / bromine / acetic acid / 3 h / Ambient temperature

3: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene

4: 92 percent / boron tribromide / hexane; CH₂Cl₂ / 0.5 h / Heating

5: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature

6: 1) acetic anhydride, sodium acetate, 2) 48percent aq. hydrogen bromide / 1) reflux, 3 h, 2) acetic acid, reflux, 0.5 h

With hydrogen bromide; bromine; sodium ethanolate; sodium acetate; acetic anhydride; boron tribromide; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In diethyl ether; ethanol; hexane; dichloromethane; acetic acid; benzene;

upstream raw materials:

6-benzylidene-3-hydroxy-4-phenyl-pyran-2,5-dione

3-hydroxy-1,4-diphenyl-2-butanone

phenylacetaldehyde

α-<(trimethylsilyl)oxy>benzenepropanenitrile