5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

Base Information

• Chemical Name: 5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane
• CAS No.: 179618-59-8
• Molecular Formula: C₂₅H₃₈O₄
• Molecular Weight: 402.574
• Mol file: 179618-59-8.mol

Synonyms:5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

Chemical Property of 5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

There total 8 articles about 5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane 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:

4-((4-methoxybenzyl)oxy)butanal (119649-27-3) + [(E)-3-Methyl-5-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-pent-2-enyl]-phosphonic acid diethyl ester (179618-58-7) → 5-[(3E,5Z)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane + 5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane (179618-59-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 1.5h; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0040-4020(96)00899-X

Reference yield:

Geraniol (106-24-1) → 5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane (179618-59-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 39 percent / potassium peroxomonosulfate, KHSO₃ / CH₂Cl₂; acetone; H₂O / 2 h / 0 °C / KH₂PO₄ and Na₂HPO₄ buffer, pH 7.5

2: 67 percent / TsOH*H₂O / H₂O / 2 h

3: CBr₄, PPh₃ / CH₂Cl₂ / 1 h / 0 °C

4: benzene / 2.5 h / Heating

5: t-BuOK / tetrahydrofuran / 1.5 h

With potassium bisulfite; oxone; carbon tetrabromide; potassium tert-butylate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetone; benzene;

DOI:10.1016/0040-4020(96)00899-X

Reference yield:

(E)-3-methyl-5-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol (124150-94-3) → 5-[(3E,5E)-9-(4-Methoxy-benzyloxy)-3-methyl-nona-3,5-dienyl]-2,2,4,4-tetramethyl-[1,3]dioxolane (179618-59-8)

Guidance literature:

Multi-step reaction with 3 steps

1: CBr₄, PPh₃ / CH₂Cl₂ / 1 h / 0 °C

2: benzene / 2.5 h / Heating

3: t-BuOK / tetrahydrofuran / 1.5 h

With carbon tetrabromide; potassium tert-butylate; triphenylphosphine; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/0040-4020(96)00899-X

upstream raw materials:

4-((4-methoxybenzyl)oxy)butanal

[(E)-3-Methyl-5-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-pent-2-enyl]-phosphonic acid diethyl ester

Geraniol

(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol

Downstream raw materials:

(6E,8E)-12-(4-Methoxy-benzyloxy)-2,6-dimethyl-dodeca-6,8-diene-2,3-diol

curacin A

(4E,6E)-10-(4-Methoxy-benzyloxy)-4-methyl-deca-4,6-dienal

(4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene