6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde

Base Information

• Chemical Name: 6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde
• CAS No.: 1114515-57-9
• Molecular Formula: C₁₉H₁₆O₅
• Molecular Weight: 324.333
• Mol file: 1114515-57-9.mol

Synonyms:6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde

Chemical Property of 6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde

There total 9 articles about 6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde 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: 97.0%

2-(6,7-methylenedioxy-3,4-diydronaphthyl)boronic acid pinacol ester (1114515-36-4) + 6-bromo-2-hydroxy-3-methoxybenzaldehyde (20035-41-0) → 6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde (1114515-57-9)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; In methanol; N,N-dimethyl-formamide; at 80 ℃; for 0.5 - 1h;

DOI:10.1016/j.tetlet.2008.11.076

Reference yield: 96.0%

2-(6,7-methylenedioxy-3,4-diydronaphthyl)boronic acid pinacol ester (1114515-36-4) + 2-acetyloxy-3-methoxy-6-bromobenzaldehyde (159263-87-3) → 6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde (1114515-57-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In methanol; N,N-dimethyl-formamide; at 80 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2010.11.066

Reference yield:

3,4-dihydro-6,7-methylenedioxy-2-trifluoromethanesulfonyloxynaphthalene (1114515-47-7) → 6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde (1114515-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C

2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; potassium carbonate; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; 2: Suzuki-Miyaura reaction;

DOI:10.1016/j.tet.2010.11.066

upstream raw materials:

2-(6,7-methylenedioxy-3,4-diydronaphthyl)boronic acid pinacol ester

6-bromo-2-hydroxy-3-methoxybenzaldehyde

3,4-dihydro-6,7-methylenedioxy-2-trifluoromethanesulfonyloxynaphthalene

2-acetyloxy-3-methoxy-6-bromobenzaldehyde

Downstream raw materials:

6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde O-methyloxime

2-acetoxy-6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-3-methoxybenzaldehyde O-methyloxime