3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran

Base Information

• Chemical Name: 3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran
• CAS No.: 144735-73-9
• Molecular Formula: C₁₉H₁₉NO₇
• Molecular Weight: 373.362

Synonyms:3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran

Chemical Property of 3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran

Chemical Property:

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Technology Process of 3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran

There total 12 articles about 3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran 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: 82.0%

3-nitro-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran (144735-72-8) → 3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran (144735-73-9)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

DOI:10.1021/jo00052a046

Reference yield:

vanillin (121-33-5,8014-42-4) → 3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran (144735-73-9)

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: 72 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

5: 80 percent / pyridine / 18 h / Ambient temperature

6: 67 percent / gl. HOAc, HNO₃ / 1) 0 deg C, 20 min, 2) RT, 2 h

7: 94 percent / H₂ / 5percent Pd-C / tetrahydrofuran / 56 h / Ambient temperature

8: 82 percent / 1N NaOH / methanol / Ambient temperature

With pyrrolidine; pyridine; ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; hydrogen; bromine; nitric acid; 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) → 3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran (144735-73-9)

Guidance literature:

Multi-step reaction with 7 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: 72 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

4: 80 percent / pyridine / 18 h / Ambient temperature

5: 67 percent / gl. HOAc, HNO₃ / 1) 0 deg C, 20 min, 2) RT, 2 h

6: 94 percent / H₂ / 5percent Pd-C / tetrahydrofuran / 56 h / Ambient temperature

7: 82 percent / 1N NaOH / methanol / Ambient temperature

With pyrrolidine; pyridine; ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; hydrogen; nitric acid; copper(II) sulfate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/jo00052a046

upstream raw materials:

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

vanillin

4-benzyloxy-3-methoxyacetophenone

5-bromo-4-hydroxy-3-methoxybenzaldehyde

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