5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Base Information

• Chemical Name: 5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde
• CAS No.: 144735-60-4
• Molecular Formula: C₂₀H₁₈O₇
• Molecular Weight: 370.359

Synonyms:5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Chemical Property of 5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Chemical Property:

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Technology Process of 5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

There total 10 articles about 5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde 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: 75.0%

5-(2-(methoxycarbonyl)ethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-59-1) → 5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-60-4)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

DOI:10.1021/jo00052a046

Reference yield:

vanillin (121-33-5,8014-42-4) → 5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-60-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / Br₂, HOAc / 1 h / Ambient temperature

2: 98 percent / pyrrolidine / pyridine / 6 h / 100 °C

3: 1) CuSO₄*H₂O, NH₄OH, NH₂OH*HCl, 2) pyridine / 1) THF, EtOH, 2) 115 deg C, 20 h

4: 92 percent / H₂ / 5percent Pd-C / tetrahydrofuran / 10 h / Ambient temperature

5: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) GH₂O, EtOH, 50 deg C, 30 min

6: 75 percent / 1N NaOH / methanol / Ambient temperature

With pyrrolidine; pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; potassium chloride; hydroxylamine hydrochloride; hydrogen; bromine; copper(II) sulfate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/jo00052a046

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → 5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-60-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / pyrrolidine / pyridine / 6 h / 100 °C

2: 1) CuSO₄*H₂O, NH₄OH, NH₂OH*HCl, 2) pyridine / 1) THF, EtOH, 2) 115 deg C, 20 h

3: 92 percent / H₂ / 5percent Pd-C / tetrahydrofuran / 10 h / Ambient temperature

4: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) GH₂O, EtOH, 50 deg C, 30 min

5: 75 percent / 1N NaOH / methanol / Ambient temperature

With pyrrolidine; pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; potassium chloride; hydroxylamine hydrochloride; hydrogen; copper(II) sulfate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/jo00052a046

upstream raw materials:

5-(2-(methoxycarbonyl)ethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

vanillin

4-benzyloxy-3-methoxyacetophenone

5-bromo-4-hydroxy-3-methoxybenzaldehyde

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