(E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene)

Base Information

• Chemical Name: (E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene)
• CAS No.: 1595276-23-5
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.461
• Mol file: 1595276-23-5.mol

Synonyms:(E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene)

Chemical Property of (E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene)

There total 6 articles about (E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene) 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:

3,3-bis(3,4-dimethoxyphenyl)-2-methylpropanal + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → (E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene) (1595276-23-5) + (Z)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene) (1595276-12-2)

Guidance literature:

(methoxymethyl)triphenylphosphonium chloride; With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at 0 ℃; Inert atmosphere;

3,3-bis(3,4-dimethoxyphenyl)-2-methylpropanal; In tetrahydrofuran; diethyl ether; at 0 ℃; for 4h; Overall yield = 420 mg; Inert atmosphere;

DOI:10.1002/anie.201307659

Reference yield:

C22H30O6 → (E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene) (1595276-23-5) + (Z)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene) (1595276-12-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium periodate / methanol; water / 5 h / 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / diethyl ether; tetrahydrofuran / 0 °C / Inert atmosphere

2.2: 4 h / 0 °C / Inert atmosphere

With sodium periodate; sodium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1002/anie.201307659

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (E)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene) (1595276-23-5) + (Z)-4,4'-(4-methoxy-2-methylbut-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene) (1595276-12-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / methanol / Inert atmosphere

2.1: phenyl[(trifluoromethane)sulfonyloxy]-lambda-3-iodanyl trifluoromethanesulfonate / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

4.1: 4-methylmorpholine N-oxide; water; osmium(VIII) oxide / tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere

5.1: sodium periodate / methanol; water / 5 h / 20 °C / Inert atmosphere

6.1: sodium hexamethyldisilazane / diethyl ether; tetrahydrofuran / 0 °C / Inert atmosphere

6.2: 4 h / 0 °C / Inert atmosphere

With sodium periodate; osmium(VIII) oxide; phenyl[(trifluoromethane)sulfonyloxy]-lambda-3-iodanyl trifluoromethanesulfonate; water; sodium hexamethyldisilazane; potassium carbonate; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 3.1: |Friedel-Crafts Alkylation;

DOI:10.1002/anie.201307659

upstream raw materials:

(methoxymethyl)triphenylphosphonium chloride

3,4-dimethoxy-benzaldehyde

(R,E)-4,4'-(2-methylpent-3-ene-1,1-diyl)bis(1,2-dimethoxybenzene)

Downstream raw materials:

(7'R,8'S)-3',4',4,5-tetramethoxy-2,7'-cyclolignan-7-ene