Phenol,4-[5-[(1E)-3-hydroxy-1-propen-1-yl]-7-methoxy-2-benzofuranyl]-2-methoxy-

Base Information

• Chemical Name: Phenol,4-[5-[(1E)-3-hydroxy-1-propen-1-yl]-7-methoxy-2-benzofuranyl]-2-methoxy-
• CAS No.: 156398-61-7
• Molecular Formula: C₁₉H₁₈O₅
• Molecular Weight: 326.349
• Mol file: 156398-61-7.mol

Synonyms:Phenol,4-[5-(3-hydroxy-1-propenyl)-7-methoxy-2-benzofuranyl]-2-methoxy-, (E)-; Phenol,4-[5-[(1E)-3-hydroxy-1-propenyl]-7-methoxy-2-benzofuranyl]-2-methoxy- (9CI);Ailanthoidol

Chemical Property of Phenol,4-[5-[(1E)-3-hydroxy-1-propen-1-yl]-7-methoxy-2-benzofuranyl]-2-methoxy-

Chemical Property:

• Melting Point: 199-201 °C
• Boiling Point: 539.2±45.0 °C(Predicted)
• PSA: 72.06000
• Density: 1.272±0.06 g/cm3(Predicted)
• LogP: 3.82810

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of Phenol,4-[5-[(1E)-3-hydroxy-1-propen-1-yl]-7-methoxy-2-benzofuranyl]-2-methoxy-

There total 43 articles about Phenol,4-[5-[(1E)-3-hydroxy-1-propen-1-yl]-7-methoxy-2-benzofuranyl]-2-methoxy- 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: 98.0%

(E)-3-(2-(4-acetoxy-3-methoxyphenyl)-7-methoxybenzofuran-5-yl)allyl acetate → (E)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxyprop-1-enyl)-7-methoxybenzofuran (156398-61-7)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0037-1610169

Reference yield: 97.0%

2-(p-hydroxy-m-methoxyphenyl)-7-methoxy-5-(carbethoxy-1-propen-1-yl)benzo[b]furan (213970-71-9) → (E)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxyprop-1-enyl)-7-methoxybenzofuran (156398-61-7)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1021/jo0258960

Reference yield: 95.0%

C21H20O6 → (E)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxyprop-1-enyl)-7-methoxybenzofuran (156398-61-7)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1002/ejoc.201600154

upstream raw materials:

2-(p-hydroxy-m-methoxyphenyl)-7-methoxy-5-(carbethoxy-1-propen-1-yl)benzo[b]furan

5-bromo-7-methoxy-2-nitrobenzofuran

5-bromo-3-methoxysalicylaldehyde

5-(2-(ethoxycarbonyl)-E-ethenyl)-7-methoxy-2-(3-methoxy-4-benzyloxyphenyl)benzofuran

Refernces

An expeditious and convergent synthesis of ailanthoidol

10.1016/j.tetlet.2010.02.018

The research presents a concise and efficient method for synthesizing ailanthoidol, a neolignan compound with various biological properties, starting from vanillin. The key reaction in this synthesis is the intramolecular Wittig reaction, which facilitates the formation of the benzofuran core of ailanthoidol. The researchers optimized the synthesis process to achieve high yields and selectivity, particularly in the intermolecular Wittig reaction step, by studying the effects of different solvents and temperatures. The overall yield of ailanthoidol was 61%, and the synthesis involved minimal protection steps and utilized readily available reagents. This approach offers a simplified and environmentally friendly alternative to previously reported methods that often involve toxic reagents and more cumbersome procedures.

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