2-Hydroxy-6-(4-hydroxy-3-methoxy-benzyl)-8-(4-hydroxy-3-methoxy-phenyl)-7-methyl-[1,4]naphthoquinone

Base Information

• Chemical Name: 2-Hydroxy-6-(4-hydroxy-3-methoxy-benzyl)-8-(4-hydroxy-3-methoxy-phenyl)-7-methyl-[1,4]naphthoquinone
• CAS No.: 133593-80-3
• Molecular Formula: C₂₆H₂₂O₇
• Molecular Weight: 446.456

Synonyms:

Chemical Property of 2-Hydroxy-6-(4-hydroxy-3-methoxy-benzyl)-8-(4-hydroxy-3-methoxy-phenyl)-7-methyl-[1,4]naphthoquinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Hydroxy-6-(4-hydroxy-3-methoxy-benzyl)-8-(4-hydroxy-3-methoxy-phenyl)-7-methyl-[1,4]naphthoquinone

There total 21 articles about 2-Hydroxy-6-(4-hydroxy-3-methoxy-benzyl)-8-(4-hydroxy-3-methoxy-phenyl)-7-methyl-[1,4]naphthoquinone 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-bromo-2-methyloxybenzaldehyde (88275-87-0) → 2-Hydroxy-6-(4-hydroxy-3-methoxy-benzyl)-8-(4-hydroxy-3-methoxy-phenyl)-7-methyl-[1,4]naphthoquinone (133593-80-3)

Guidance literature:

Multi-step reaction with 20 steps

1: 91 percent / benzene / 20 h / Heating

2: 95 percent / 90percent aq. CF₃COOH / 0.25 h / 25 °C

3: 84 percent / AcOK / 0.08 h / Heating

4: 94 percent / diisobutylaluminium hydride / tetrahydrofuran / -10 °C

5: 82 percent / K₂CO₃ / dimethylformamide / 96 h / 25 °C

6: 90 percent / MnO₂ / CH₂Cl₂ / 12 h / 25 °C

7: p-ClC₆H₄CO₃H / CH₂Cl₂ / 72 h / Heating

8: NaOMe, MeOH / 0.08 h

9: K₂CO₃ / dimethylformamide / 72 h / 50 °C

10: 95 percent / dimethylformamide / 12 h / Heating

11: 85 percent / NaOH / methanol; H₂O / 96 h / Heating

12: (COCl)2 / CH₂Cl₂ / 2.5 h / 25 °C

13: CH₂Cl₂ / 2 h / 25 °C

14: SOCl₂ / CH₂Cl₂ / 2 h / 25 °C

15: 88 percent / tetrahydrofuran / 0.75 h / 25 °C

16: 1.) BuLi, TMEDA / 1.) THF, -78 deg C, 1 h

17: HCl / dioxane / 0.5 h / Heating

18: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / 25 °C

19: 80 percent / H₂, Et₃N, (CF₃CO)2O / Pd/C / tetrahydrofuran / 18 h

20: 1.) BCl₃, 2.) KOH, air / 1.) CH₂Cl₂, -10 deg C, 8 h, 2.) EtOH/EtOAc, 30 s

With hydrogenchloride; methanol; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; air; N,N,N,N,-tetramethylethylenediamine; p-chloroperbenzoic acid; hydrogen; sodium methylate; potassium acetate; boron trichloride; diisobutylaluminium hydride; potassium carbonate; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39910000190

Reference yield:

7-Bromo-4-isopropoxy-8-methoxy-naphthalen-2-ol → 2-Hydroxy-6-(4-hydroxy-3-methoxy-benzyl)-8-(4-hydroxy-3-methoxy-phenyl)-7-methyl-[1,4]naphthoquinone (133593-80-3)

Guidance literature:

Multi-step reaction with 12 steps

1: K₂CO₃ / dimethylformamide / 72 h / 50 °C

2: 95 percent / dimethylformamide / 12 h / Heating

3: 85 percent / NaOH / methanol; H₂O / 96 h / Heating

4: (COCl)2 / CH₂Cl₂ / 2.5 h / 25 °C

5: CH₂Cl₂ / 2 h / 25 °C

6: SOCl₂ / CH₂Cl₂ / 2 h / 25 °C

7: 88 percent / tetrahydrofuran / 0.75 h / 25 °C

8: 1.) BuLi, TMEDA / 1.) THF, -78 deg C, 1 h

9: HCl / dioxane / 0.5 h / Heating

10: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / 25 °C

11: 80 percent / H₂, Et₃N, (CF₃CO)2O / Pd/C / tetrahydrofuran / 18 h

12: 1.) BCl₃, 2.) KOH, air / 1.) CH₂Cl₂, -10 deg C, 8 h, 2.) EtOH/EtOAc, 30 s

With hydrogenchloride; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; air; N,N,N,N,-tetramethylethylenediamine; hydrogen; boron trichloride; potassium carbonate; triethylamine; trifluoroacetic anhydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c39910000190

Reference yield:

6-Bromo-3-(hydroxymethyl)-5-methoxy-1-naphthol (133593-69-8) → 2-Hydroxy-6-(4-hydroxy-3-methoxy-benzyl)-8-(4-hydroxy-3-methoxy-phenyl)-7-methyl-[1,4]naphthoquinone (133593-80-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 82 percent / K₂CO₃ / dimethylformamide / 96 h / 25 °C

2: 90 percent / MnO₂ / CH₂Cl₂ / 12 h / 25 °C

3: p-ClC₆H₄CO₃H / CH₂Cl₂ / 72 h / Heating

4: NaOMe, MeOH / 0.08 h

5: K₂CO₃ / dimethylformamide / 72 h / 50 °C

6: 95 percent / dimethylformamide / 12 h / Heating

7: 85 percent / NaOH / methanol; H₂O / 96 h / Heating

8: (COCl)2 / CH₂Cl₂ / 2.5 h / 25 °C

9: CH₂Cl₂ / 2 h / 25 °C

10: SOCl₂ / CH₂Cl₂ / 2 h / 25 °C

11: 88 percent / tetrahydrofuran / 0.75 h / 25 °C

12: 1.) BuLi, TMEDA / 1.) THF, -78 deg C, 1 h

13: HCl / dioxane / 0.5 h / Heating

14: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / 25 °C

15: 80 percent / H₂, Et₃N, (CF₃CO)2O / Pd/C / tetrahydrofuran / 18 h

16: 1.) BCl₃, 2.) KOH, air / 1.) CH₂Cl₂, -10 deg C, 8 h, 2.) EtOH/EtOAc, 30 s

With hydrogenchloride; methanol; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; air; N,N,N,N,-tetramethylethylenediamine; p-chloroperbenzoic acid; hydrogen; sodium methylate; boron trichloride; potassium carbonate; triethylamine; trifluoroacetic anhydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c39910000190

upstream raw materials:

1-(4-Isopropoxy-3-methoxyphenyl)-3-(4-isopropoxy-3-methoxybenzyl)-5,7-diisopropoxy-2-methylnaphthalene

3-bromo-2-methyloxybenzaldehyde

6-Bromo-3-(hydroxymethyl)-5-methoxy-1-naphthol

(7-Bromo-4-isopropoxy-8-methoxy-2-naphthyl)methanol

Downstream raw materials:

larreantin

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