4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane

Base Information

• Chemical Name: 4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane
• CAS No.: 1372559-96-0
• Molecular Formula: C₂₅H₂₄O₃
• Molecular Weight: 372.464
• Mol file: 1372559-96-0.mol

Synonyms:4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane

Chemical Property of 4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane

There total 3 articles about 4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane 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: 87.0%

ortho-methoxymethyleneoxyphenylboronic acid (115377-93-0) + 4-bromo-16-carboxaldehyde-[2.2]paracyclophane (320749-00-6) → 4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane (1372559-96-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In toluene; for 20h; Inert atmosphere; Reflux;

DOI:10.1002/ijch.201100096

Reference yield:

[2.2]Paracyclophan (1633-22-3) → 4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane (1372559-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: bromine / tetrachloromethane / 2 h / 60 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 20 h / Inert atmosphere; Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; n-butyllithium; bromine; In tetrahydrofuran; tetrachloromethane; hexane; toluene; 3.1: Suzuki coupling;

DOI:10.1002/ijch.201100096

Reference yield:

4,16-dibromo[2.2]paracyclophane (196316-30-0,196316-31-1,23927-40-4,96392-77-7) → 4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane (1372559-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 20 h / Inert atmosphere; Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; n-butyllithium; In tetrahydrofuran; hexane; toluene; 2.1: Suzuki coupling;

DOI:10.1002/ijch.201100096

upstream raw materials:

[2.2]Paracyclophan

4,16-dibromo[2.2]paracyclophane

ortho-methoxymethyleneoxyphenylboronic acid

4-bromo-16-carboxaldehyde-[2.2]paracyclophane

Downstream raw materials:

4-formyl-12-(2-hydroxyphenyl)-[2.2]paracyclophane

C₂₅H₂₅NO₂

Refernces