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

Base Information

• Chemical Name: 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-carbaldehyde
• CAS No.: 135040-89-0
• Molecular Formula: C₂₂H₂₂O₇
• Molecular Weight: 398.412

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

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

Chemical Property:

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

There total 16 articles about 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-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: 10.0%

dicyanozinc (557-21-1) + 2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxybenzofuran (135040-88-9) → 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (135040-90-3) + 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-carbaldehyde (135040-89-0)

Guidance literature:

With hydrogenchloride; potassium chloride; In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(00)78908-8

Reference yield:

5-(2-(methoxycarbonyl)trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (144735-55-7) → 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-carbaldehyde (135040-89-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / H₂ / 5percent Pd-C / tetrahydrofuran / 10 h / Ambient temperature

2: 82 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

3: 91 percent / pyridine / 18 h / Ambient temperature

4: 85 percent / 10N NH₄OH / acetone / 0.67 h / Ambient temperature

5: 1) HCl, KCl / 1) Et₂O, 0 deg C, 2) EtOH, H₂O, 50 deg C, 30 min

With pyridine; hydrogenchloride; ammonium hydroxide; lithium aluminium tetrahydride; potassium chloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; acetone;

DOI:10.1021/jo00052a046

Reference yield:

vanillin (121-33-5,8014-42-4) → 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-carbaldehyde (135040-89-0)

Guidance literature:

Multi-step reaction with 8 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: 82 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

6: 91 percent / pyridine / 18 h / Ambient temperature

7: 85 percent / 10N NH₄OH / acetone / 0.67 h / Ambient temperature

8: 1) HCl, KCl / 1) Et₂O, 0 deg C, 2) EtOH, H₂O, 50 deg C, 30 min

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

DOI:10.1021/jo00052a046

upstream raw materials:

dicyanozinc

2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxybenzofuran

vanillin

4-benzyloxy-3-methoxyacetophenone

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