(Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester

Base Information

Chemical Name:(Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester
CAS No.:467217-12-5
Molecular Formula:C₂₂H₃₀O₃
Molecular Weight:342.478
Hs Code.:

Synonyms:(Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester

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Chemical Property of (Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester

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Technology Process of (Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester

There total 12 articles about (Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester 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: 96.0%

: 467217-04-5
(Z)-6-{3-[(3Z,6Z)-1-(tert-Butyl-diphenyl-silanyloxy)-nona-3,6-dienyl]-phenyl}-hex-5-enoic acid methyl ester

: 467217-12-5
(Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 15h;
DOI:10.1016/S0040-4039(02)01056-0

Reference yield:

: 626-19-7
Isophthalaldehyde

: 467217-12-5
(Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 90 percent / NH₄NO₃ / methanol / 2 h / Heating

2: 88 percent / SiO₂; aq. H₂SO₄ / CH₂Cl₂ / 0.75 h / 20 °C

3: 79 percent / LDA / tetrahydrofuran / 0.5 h / -80 °C

4: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C

5: 50 percent / DIBAL-H / diethyl ether / 1.5 h / -60 °C

6: 78 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 4 h / -80 °C

7: 100 percent / SiO₂; aq. H₂SO₄ / CH₂Cl₂ / 1.5 h / 20 °C

8: LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.5 h / -80 °C

9: Na₂CO₃ / hexamethylphosphoric acid triamide; tetrahydrofuran / 12 h / 20 °C

10: 96 percent / nBu₄NF / tetrahydrofuran / 15 h / 0 - 20 °C

With 1H-imidazole; ammonium nitrate; n-butyllithium; sulfuric acid; tetrabutyl ammonium fluoride; silica gel; diisobutylaluminium hydride; sodium carbonate; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 6: Swern oxidation / 7: Wittig reaction / 9: Wittig reaction;
DOI:10.1016/S0040-4039(02)01056-0

Reference yield:

: 37832-33-0
isophthalaldehyde bis-dimethylacetal

: 467217-12-5
(Z)-6-[3-((3Z,6Z)-1-Hydroxy-nona-3,6-dienyl)-phenyl]-hex-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / SiO₂; aq. H₂SO₄ / CH₂Cl₂ / 0.75 h / 20 °C

2: 79 percent / LDA / tetrahydrofuran / 0.5 h / -80 °C

3: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C

4: 50 percent / DIBAL-H / diethyl ether / 1.5 h / -60 °C

5: 78 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 4 h / -80 °C

6: 100 percent / SiO₂; aq. H₂SO₄ / CH₂Cl₂ / 1.5 h / 20 °C

7: LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.5 h / -80 °C

8: Na₂CO₃ / hexamethylphosphoric acid triamide; tetrahydrofuran / 12 h / 20 °C

9: 96 percent / nBu₄NF / tetrahydrofuran / 15 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; sulfuric acid; tetrabutyl ammonium fluoride; silica gel; diisobutylaluminium hydride; sodium carbonate; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5: Swern oxidation / 6: Wittig reaction / 8: Wittig reaction;
DOI:10.1016/S0040-4039(02)01056-0