ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate

Base Information

• Chemical Name: ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate
• CAS No.: 173446-84-9
• Molecular Formula: C₂₄H₃₄O₃
• Molecular Weight: 370.532
• Mol file: 173446-84-9.mol

Synonyms:ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate

Chemical Property of ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate

There total 10 articles about ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate 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: 75.0%

ethyl 2-methoxy-6-[8(Z),11(Z),14-pentadecatrienyl]benzoate (332011-48-0) → ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate (173446-84-9)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1248/cpb.49.18

Reference yield:

8-bromooctanol (50816-19-8) → ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate (173446-84-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 90.2 percent / SOCl₂; pyridine / benzene / 7 h / 75 °C

2.1: BuLi; HMPA / hexane; tetrahydrofuran / 0.5 h / 0 °C

2.2: 89.4 percent / hexane; tetrahydrofuran / 1 h / 0 °C

3.1: 77.3 percent / hydroquinone; aq. H₃PO₄ / dioxane / 4.5 h / 100 °C

4.1: 60.8 percent / methanol / 1.5 h / 20 °C

5.1: 79.5 percent / Ag₂O / CH₂Cl₂ / 24 h / 20 °C

6.1: 95.4 percent / NaI / acetone / 24 h / Heating

7.1: 82.4 percent / NaHCO₃; DMSO / 11 h / 90 °C

8.1: BuLi / hexane; tetrahydrofuran / 1 h / 20 °C

8.2: 69.3 percent / tetrahydrofuran / 0.5 h / 20 °C

9.1: 75 percent / BBr₃ / CH₂Cl₂ / 1 h / 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; thionyl chloride; phosphoric acid; boron tribromide; sodium hydrogencarbonate; dimethyl sulfoxide; hydroquinone; sodium iodide; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetone; benzene; 9.2: Wittig reaction;

DOI:10.1248/cpb.49.18

Reference yield:

1-bromo-8-chloro-octane (28598-82-5) → ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate (173446-84-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: BuLi; HMPA / hexane; tetrahydrofuran / 0.5 h / 0 °C

1.2: 89.4 percent / hexane; tetrahydrofuran / 1 h / 0 °C

2.1: 77.3 percent / hydroquinone; aq. H₃PO₄ / dioxane / 4.5 h / 100 °C

3.1: 60.8 percent / methanol / 1.5 h / 20 °C

4.1: 79.5 percent / Ag₂O / CH₂Cl₂ / 24 h / 20 °C

5.1: 95.4 percent / NaI / acetone / 24 h / Heating

6.1: 82.4 percent / NaHCO₃; DMSO / 11 h / 90 °C

7.1: BuLi / hexane; tetrahydrofuran / 1 h / 20 °C

7.2: 69.3 percent / tetrahydrofuran / 0.5 h / 20 °C

8.1: 75 percent / BBr₃ / CH₂Cl₂ / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; phosphoric acid; boron tribromide; sodium hydrogencarbonate; dimethyl sulfoxide; hydroquinone; sodium iodide; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetone; 8.2: Wittig reaction;

DOI:10.1248/cpb.49.18

upstream raw materials:

ethyl 2-methoxy-6-[8(Z),11(Z),14-pentadecatrienyl]benzoate

8-bromooctanol

1-bromo-8-chloro-octane

ethyl 6-(7-formylheptyl)-2-methoxybenzoate

Downstream raw materials:

6-(8(Z),11(Z),14-pentadecatrienyl)salicylic acid

Refernces