Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate

Base Information

• Chemical Name: Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate
• CAS No.: 164981-05-9
• Molecular Formula: C₂₅H₃₂O₃
• Molecular Weight: 380.527
• Mol file: 164981-05-9.mol

Synonyms:Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate

Chemical Property of Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate

There total 11 articles about Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate 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: 91.0%

6-{3-[(tert-butyl-dimethyl-silanyloxy)-(4-pentyl-phenyl)-methyl]-phenyl}-hex-5-enoic acid methyl ester → Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate (164981-05-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 15h;

DOI:10.1016/S0040-4039(02)01056-0

Reference yield:

Isophthalaldehyde (626-19-7) → Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate (164981-05-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / NH₄NO₃ / methanol / 2 h / Heating

2.1: 88 percent / SiO₂; aq. H₂SO₄ / CH₂Cl₂ / 0.75 h / 20 °C

3.1: nBuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.5 h / -80 °C

3.2: secBuLi / tetrahydrofuran / -80 °C

4.1: 92 percent / imidazole / dimethylformamide / 15 h / 20 °C

5.1: 92 percent / H₂ / Pd/C / ethyl acetate / 0.5 h / 20 °C

6.1: 100 percent / SiO₂; aq. H₂SO₄ / CH₂Cl₂ / 1.5 h / 20 °C

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

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

9.1: 91 percent / nBu₄NF / tetrahydrofuran / 15 h / 0 - 20 °C

With 1H-imidazole; ammonium nitrate; n-butyllithium; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; silica gel; sodium carbonate; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 7.1: Wittig reaction;

DOI:10.1016/S0040-4039(02)01056-0

Reference yield:

isophthalaldehyde bis-dimethylacetal (37832-33-0) → Methyl(5Z)-6-{3-[hydroxy-(4-pentylphenyl)methyl]phenyl}hex-5-enoate (164981-05-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 88 percent / SiO₂; aq. H₂SO₄ / CH₂Cl₂ / 0.75 h / 20 °C

2.1: nBuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.5 h / -80 °C

2.2: secBuLi / tetrahydrofuran / -80 °C

3.1: 92 percent / imidazole / dimethylformamide / 15 h / 20 °C

4.1: 92 percent / H₂ / Pd/C / ethyl acetate / 0.5 h / 20 °C

5.1: 100 percent / SiO₂; aq. H₂SO₄ / CH₂Cl₂ / 1.5 h / 20 °C

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

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

8.1: 91 percent / nBu₄NF / tetrahydrofuran / 15 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; silica gel; sodium carbonate; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 6.1: Wittig reaction;

DOI:10.1016/S0040-4039(02)01056-0

upstream raw materials:

Isophthalaldehyde

isophthalaldehyde bis-dimethylacetal

(4-carboxybutyl)triphenylphosphonium bromide

3-(dimethoxymethyl)benzaldehyde