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

Base Information

• Chemical Name: 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-carbaldehyde
• CAS No.: 144735-77-3
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375
• Mol file: 144735-77-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 5-(3-hydroxypropyl)-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: 55.0%

2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxybenzofurane (144735-57-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-carbaldehyde (144735-77-3)

Guidance literature:

With trichlorophosphate; 1) RT, 30 min, 2) 1.5 h, boiling, 3) RT, overnight;

DOI:10.1021/jo00052a046

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-carbaldehyde (144735-77-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 63 percent / POCl₃ / 1) 0 deg C, 20 min, 2) 65 deg C, 10 h

2: 79 percent / NaOH / H₂O; dioxane / 2 h / 80 °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: 55 percent / POCl₃ / 1) RT, 30 min, 2) 1.5 h, boiling, 3) RT, overnight

With pyridine; ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; hydrogen; copper(II) sulfate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jo00052a046

Reference yield:

vanillin (121-33-5,8014-42-4) → 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-4-carbaldehyde (144735-77-3)

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

6: 55 percent / POCl₃ / 1) RT, 30 min, 2) 1.5 h, boiling, 3) RT, overnight

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

DOI:10.1021/jo00052a046

upstream raw materials:

2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxybenzofurane

N,N-dimethyl-formamide

4-benzyloxy-3-methoxyacetophenone

vanillin

Refernces