2,4,6-Octatrien-1-one, 8-[(4-methoxyphenyl)methoxy]-1-phenyl-, (E,E,E)-

Base Information

• Chemical Name: 2,4,6-Octatrien-1-one, 8-[(4-methoxyphenyl)methoxy]-1-phenyl-, (E,E,E)-
• CAS No.: 139591-44-9
• Molecular Formula: C22H22O3
• Molecular Weight: 334.415
• Mol file: 139591-44-9.mol

Synonyms:

Chemical Property of 2,4,6-Octatrien-1-one, 8-[(4-methoxyphenyl)methoxy]-1-phenyl-, (E,E,E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,6-Octatrien-1-one, 8-[(4-methoxyphenyl)methoxy]-1-phenyl-, (E,E,E)-

There total 10 articles about 2,4,6-Octatrien-1-one, 8-[(4-methoxyphenyl)methoxy]-1-phenyl-, (E,E,E)- 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:

cyclobut-3-ene-1,2-dicarboxylic acid anhydride (10374-07-9) → 1-phenyl-8-<(4-methoxyphenyl)methoxy>-octa-2E,4E,6E-trien-1-one (139591-44-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 0.5 h, 2) reflux, 72 h

2: 75 percent / pyridinium dichromate, oxalic acid / CH₂Cl₂ / 4 h / Ambient temperature

3: 83 percent / TiCl₄ / CH₂Cl₂ / 1 h / Ambient temperature

4: 50 percent / 1) KH, 18-crown-6 / tetrahydrofuran / 16 h / Ambient temperature

5: CH₃I, Na₂CO₃ / acetone; H₂O / 60 h / Ambient temperature

6: NaBH₄ / ethanol / 1.5 h / -78 °C

8: 1) n-BuLi / 1) THF,hexane, 20 min., 2) THF, 2.1) 20 deg C, 14 h, 2.2) reflux, 28 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 18-crown-6 ether; oxalic acid; titanium tetrachloride; potassium hydride; sodium carbonate; methyl iodide; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)89013-X

Reference yield:

(1R,4S)-(4-hydroxymethylcyclobut-2-enyl)methanol (77774-01-7,446840-28-4) → 1-phenyl-8-<(4-methoxyphenyl)methoxy>-octa-2E,4E,6E-trien-1-one (139591-44-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / pyridinium dichromate, oxalic acid / CH₂Cl₂ / 4 h / Ambient temperature

2: 83 percent / TiCl₄ / CH₂Cl₂ / 1 h / Ambient temperature

3: 50 percent / 1) KH, 18-crown-6 / tetrahydrofuran / 16 h / Ambient temperature

4: CH₃I, Na₂CO₃ / acetone; H₂O / 60 h / Ambient temperature

5: NaBH₄ / ethanol / 1.5 h / -78 °C

7: 1) n-BuLi / 1) THF,hexane, 20 min., 2) THF, 2.1) 20 deg C, 14 h, 2.2) reflux, 28 h

With sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; 18-crown-6 ether; oxalic acid; titanium tetrachloride; potassium hydride; sodium carbonate; methyl iodide; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)89013-X

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → 1-phenyl-8-<(4-methoxyphenyl)methoxy>-octa-2E,4E,6E-trien-1-one (139591-44-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / 1) KH, 18-crown-6 / tetrahydrofuran / 16 h / Ambient temperature

2: CH₃I, Na₂CO₃ / acetone; H₂O / 60 h / Ambient temperature

3: NaBH₄ / ethanol / 1.5 h / -78 °C

5: 1) n-BuLi / 1) THF,hexane, 20 min., 2) THF, 2.1) 20 deg C, 14 h, 2.2) reflux, 28 h

With sodium tetrahydroborate; n-butyllithium; 18-crown-6 ether; potassium hydride; sodium carbonate; methyl iodide; In tetrahydrofuran; ethanol; water; acetone;

DOI:10.1016/S0040-4020(01)89013-X

upstream raw materials:

triphenylphenacylphosphonium bromide

6-<(4-methoxyphenyl)methoxy>-(2E,4E)-hexadienal

cyclobut-3-ene-1,2-dicarboxylic acid anhydride

(1R,4S)-(4-hydroxymethylcyclobut-2-enyl)methanol

Downstream raw materials:

8-oxo-8-phenylocta-2E,4E,6E-trienal