1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene

Base Information

• Chemical Name: 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene
• CAS No.: 219630-97-4
• Molecular Formula: C₃₁H₄₄O₆
• Molecular Weight: 512.687
• Mol file: 219630-97-4.mol

Synonyms:1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene

Chemical Property of 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene

There total 18 articles about 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene 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:

1,7-dibromoheptane (4549-31-9) → 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene (219630-97-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, TMEDA, 2.) HMPA / 1.) toluene, hexane, -78 deg C, 1 h, 2.) toluene, hexane, from -78 deg C to RT, 2.5 h

2: 1.) nBuLi, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT, 4.5 h

3: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) LDA, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight

5: H₂ / Pd/BaSO₄ / pyridine / 36 h

6: 1.) 48 percent aq. HBr, 2.) O₂, NaHCO₃ / 1.) MeOH, 50 deg C, 15 min, 2.) MeOH, 30 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; hydrogen bromide; hydrogen; oxygen; sodium hydrogencarbonate; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; pyridine;

DOI:10.1248/cpb.46.1770

Reference yield:

1,3-dimethoxy-5-(7'-hydroxyheptyl)benzene (52483-31-5) → 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene (219630-97-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / Amberlist-15 / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.) n-BuLi, TMEDA / 1.) hexane, -20 deg C, 1 h, 2.) hexane, THF, RT, 4 h

3: 67 percent / p-toluenesulfonic acid, MeOH / 24 h

4: 1.3 g / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

5: 94 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 - 20 °C

6: 86 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / Ambient temperature

7: 95 percent / NaI / acetone / 48 h / Heating

8: 1.) LDA, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight

9: H₂ / Pd/BaSO₄ / pyridine / 36 h

10: 1.) 48 percent aq. HBr, 2.) O₂, NaHCO₃ / 1.) MeOH, 50 deg C, 15 min, 2.) MeOH, 30 min

With methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Amberlist-15; hydrogen bromide; hydrogen; oxygen; boron tribromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium diisopropyl amide; Pd-BaSO₄; In pyridine; dichloromethane; acetone;

DOI:10.1248/cpb.46.1770

Reference yield:

6-benzyloxy-1-hexanal (101492-91-5) → 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene (219630-97-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 3 h

2: 85 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 760 Torr

3: 96 percent / Amberlist-15 / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) n-BuLi, TMEDA / 1.) hexane, -20 deg C, 1 h, 2.) hexane, THF, RT, 4 h

5: 67 percent / p-toluenesulfonic acid, MeOH / 24 h

6: 1.3 g / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

7: 94 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 - 20 °C

8: 86 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / Ambient temperature

9: 95 percent / NaI / acetone / 48 h / Heating

10: 1.) LDA, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight

11: H₂ / Pd/BaSO₄ / pyridine / 36 h

12: 1.) 48 percent aq. HBr, 2.) O₂, NaHCO₃ / 1.) MeOH, 50 deg C, 15 min, 2.) MeOH, 30 min

With methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Amberlist-15; hydrogen bromide; hydrogen; oxygen; boron tribromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; Pd-BaSO₄; In pyridine; ethanol; dichloromethane; acetone;

DOI:10.1248/cpb.46.1770

upstream raw materials:

1,7-dibromoheptane

1,3-dimethoxy-5-(7'-hydroxyheptyl)benzene

6-benzyloxy-1-hexanal

(3,5-dimethoxybenzyl)triphenylphosphonium bromide

Downstream raw materials:

ardisiaquinone F