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

Base Information

• Chemical Name: 2-acetoxy-6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-3-methoxybenzaldehyde O-methyloxime
• CAS No.: 1114515-65-9
• Molecular Formula: C₂₂H₂₁NO₆
• Molecular Weight: 395.412
• Mol file: 1114515-65-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 2-acetoxy-6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-3-methoxybenzaldehyde O-methyloxime 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: 94.0%

6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-2-hydroxy-3-methoxybenzaldehyde O-methyloxime (1114515-63-7) + acetic anhydride (108-24-7) → 2-acetoxy-6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-3-methoxybenzaldehyde O-methyloxime (1114515-65-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 80 ℃; for 1h;

DOI:10.1016/j.tetlet.2008.11.076

Reference yield:

3,4-dihydro-6,7-methylenedioxy-2-trifluoromethanesulfonyloxynaphthalene (1114515-47-7) → 2-acetoxy-6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-3-methoxybenzaldehyde O-methyloxime (1114515-65-9)

Guidance literature:

Multi-step reaction with 4 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

3: sodium acetate / ethanol / 1 h / 80 °C

4: dmap; triethylamine / dichloromethane / 1 h / 80 °C

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

DOI:10.1016/j.tet.2010.11.066

Reference yield:

2-(6,7-methylenedioxy-3,4-diydronaphthyl)boronic acid pinacol ester (1114515-36-4) → 2-acetoxy-6-(3,4-dihydro-6,7-methylenedioxy-2-naphthyl)-3-methoxybenzaldehyde O-methyloxime (1114515-65-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2: sodium acetate / ethanol / 1 h / 80 °C

3: dmap; triethylamine / dichloromethane / 1 h / 80 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; sodium acetate; potassium carbonate; triethylamine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Suzuki-Miyaura reaction;

DOI:10.1016/j.tet.2010.11.066

upstream raw materials:

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

acetic anhydride

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

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