5-[7-[(E)-3,7-Dimethyl-2,6-octadienyl]-6-hydroxybenzofuran-2-yl]-1,3-benzenediol

Base Information

• Chemical Name: 5-[7-[(E)-3,7-Dimethyl-2,6-octadienyl]-6-hydroxybenzofuran-2-yl]-1,3-benzenediol
• CAS No.: 95378-08-8
• Molecular Formula: C24H26 O4
• Molecular Weight: 378.468
• Mol file: 95378-08-8.mol

Synonyms:1,3-Benzenediol,5-[7-(3,7-dimethyl-2,6-octadienyl)-6-hydroxy-2-benzofuranyl]-, (E)-;1,3-Benzenediol,5-[7-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-hydroxy-2-benzofuranyl]- (9CI);Mulberrofuran L; O-Demethylmulberrofuran B

Chemical Property of 5-[7-[(E)-3,7-Dimethyl-2,6-octadienyl]-6-hydroxybenzofuran-2-yl]-1,3-benzenediol

Chemical Property:

• Melting Point: 148 - 151 °C
• PSA: 73.83000
• LogP: 6.45180

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[7-[(E)-3,7-Dimethyl-2,6-octadienyl]-6-hydroxybenzofuran-2-yl]-1,3-benzenediol

There total 10 articles about 5-[7-[(E)-3,7-Dimethyl-2,6-octadienyl]-6-hydroxybenzofuran-2-yl]-1,3-benzenediol 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: 77.0%

2-(3,5-bis(ethoxymethoxy)phenyl)-7-(3,7-dimethylocta-2,6-dien-1-yl)-6-(ethoxymethoxy)benzofuran → mulberrofuran L (95378-08-8)

Guidance literature:

With Dowex resin; In methanol; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1002/bkcs.10442

Reference yield:

5-(7-(3,7-dimethylocta-2,6-dien-1-yl)-6-methoxybenzofuran-2-yl)benzene-1,3-diol (79295-49-1) → mulberrofuran L (95378-08-8)

Guidance literature:

With pyridine hydrochloride; at 215 ℃; for 0.25h;

Reference yield:

5-bromoresorcinol (106120-04-1) → mulberrofuran L (95378-08-8)

Guidance literature:

Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C / Inert atmosphere

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 11 h / 80 °C / Sealed tube; Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 48 h / 80 °C / Sealed tube; Inert atmosphere

4: Dowex resin / methanol / 72 h / 20 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 2: |Miyaura Borylation Reaction / 3: |Suzuki Coupling;

DOI:10.1002/bkcs.10442

upstream raw materials:

5-(7-(3,7-dimethylocta-2,6-dien-1-yl)-6-methoxybenzofuran-2-yl)benzene-1,3-diol

5-bromoresorcinol

2,4-Dihydroxybenzaldehyde

trans-geranyl bromide

Downstream raw materials:

mulberrofuran L trimethyl ether

5-[7-Methyl-7-(4-methyl-pent-3-enyl)-7H-furo[2,3-f]chromen-2-yl]-benzene-1,3-diol

Refernces

• 1、 Fukai, Toshio,Fujimoto, Tomoko,Hano, Yoshio,Nomura, Taro,Uzawa, Jun. "STRUCTURES OF MULBERROFURANS B AND L, 2-ARYLBENZOFURAN DERIVATIVES FROM THE ROOT BARK OF THE CULTIVATED MULBERRY TREE (MORUS LHOU (SER.) KOIDZ.)". . p. 2805 - 2814. Retrieved 2007/10/02.