5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman

Base Information

• Chemical Name: 5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman
• CAS No.: 873336-77-7
• Molecular Formula: C₂₄H₃₀O₄
• Molecular Weight: 382.5
• Mol file: 873336-77-7.mol

Synonyms:5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman

Chemical Property of 5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman

There total 2 articles about 5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman 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: 39.0%

diethyl (3,4-dimethoxybenzyl)phosphonate (78055-65-9) + 3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-carboxaldehyde (389633-98-1) → 5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman (873336-77-7)

Guidance literature:

diethyl (3,4-dimethoxybenzyl)phosphonate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-carboxaldehyde; In N,N-dimethyl-formamide; at 0 - 40 ℃; for 24.5h;

DOI:10.1002/chem.201002020

Reference yield:

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) → 5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman (873336-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / tetrabutylammonium iodide / 24 h / 110 °C

2: 36 percent / t-BuOK / dimethylformamide / 20 - 110 °C

With potassium tert-butylate; tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; 2: Horner-Emmons reaction;

DOI:10.1021/jm0506120

Reference yield: 100.0%

5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman (873336-77-7) → 5-[2-(3,4-dimethoxy-phenyl)-ethyl]-6-methoxy-2,2,7,8-tetramethyl-chroman (873336-79-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 5h; under 2585.74 Torr;

DOI:10.1021/jm0506120

upstream raw materials:

diethyl (3,4-dimethoxybenzyl)phosphonate

3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-carboxaldehyde

4-bromomethyl-1,2-dimethoxybenzene

Downstream raw materials:

5-[2-(3,4-dimethoxy-phenyl)-ethyl]-6-methoxy-2,2,7,8-tetramethyl-chroman

4-[2-(6-methoxy-2,2,7,8-tetramethyl-chroman-5-yl)-ethyl]-benzene-1,2-diol

C₂₁H₂₄O₄