2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid

Base Information

• Chemical Name: 2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid
• CAS No.: 173473-61-5
• Molecular Formula: C₂₃H₃₄O₃
• Molecular Weight: 358.521
• Mol file: 173473-61-5.mol

Synonyms:

Chemical Property of 2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid

There total 12 articles about 2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid 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:

2-Methoxy-6-(8,11-pentadecadiynyl)benzoic acid (173473-59-1) → 2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid (173473-61-5)

Guidance literature:

With quinoline; hydrogen; Pd-BaSO₄; In pyridine; Yield given; Ambient temperature;

Reference yield:

9-(2-tetrahydropyranyloxy)-1-nonyne (10160-26-6) → 2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid (173473-61-5)

Guidance literature:

Multi-step reaction with 11 steps

1: n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 30 min, 2.) r.t., 70 min

2: p-TsOH*H₂O / methanol / 1 h / Ambient temperature

3: 99 percent / pyridine / 3.5 h / Ambient temperature

4: 73 percent / dichloromaleic anhydride / 200 °C

5: 99 percent / 2 M KOH / ethanol / 19 h / Heating

6: 72 percent / CBr₄, PPh₃ / CH₂Cl₂ / 6 h / Ambient temperature

7: n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 3.5 h, 2.) -78 deg C to r.t., 17 h

8: p-TsOH*H₂O / methanol / 1 h / Heating

9: 68 percent / CBr₄, PPh₃ / diethyl ether; CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 17 h

10: 1.) EtMgBr, 2.) CuCN / 1.) THF, reflux, 1 h; r.t., 15 min, 2.) 0 deg C, 1 h; r.t., 2.75 h

11: H₂, quinoline / 5percent Pd/BaSO₄ / pyridine / Ambient temperature

With pyridine; quinoline; potassium hydroxide; n-butyllithium; dichloromaleic acid anhydride; carbon tetrabromide; ethylmagnesium bromide; hydrogen; toluene-4-sulfonic acid; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane;

Reference yield:

8-nonyn-1-ol (10160-28-8) → 2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid (173473-61-5)

Guidance literature:

Multi-step reaction with 12 steps

1: p-TsOH*H₂O / 2 h / Ambient temperature

2: n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 30 min, 2.) r.t., 70 min

3: p-TsOH*H₂O / methanol / 1 h / Ambient temperature

4: 99 percent / pyridine / 3.5 h / Ambient temperature

5: 73 percent / dichloromaleic anhydride / 200 °C

6: 99 percent / 2 M KOH / ethanol / 19 h / Heating

7: 72 percent / CBr₄, PPh₃ / CH₂Cl₂ / 6 h / Ambient temperature

8: n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 3.5 h, 2.) -78 deg C to r.t., 17 h

9: p-TsOH*H₂O / methanol / 1 h / Heating

10: 68 percent / CBr₄, PPh₃ / diethyl ether; CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 17 h

11: 1.) EtMgBr, 2.) CuCN / 1.) THF, reflux, 1 h; r.t., 15 min, 2.) 0 deg C, 1 h; r.t., 2.75 h

12: H₂, quinoline / 5percent Pd/BaSO₄ / pyridine / Ambient temperature

With pyridine; quinoline; potassium hydroxide; n-butyllithium; dichloromaleic acid anhydride; carbon tetrabromide; ethylmagnesium bromide; hydrogen; toluene-4-sulfonic acid; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane;

upstream raw materials:

2-Methoxy-6-(8,11-pentadecadiynyl)benzoic acid

9-(2-tetrahydropyranyloxy)-1-nonyne

8-nonyn-1-ol

methyl 10-<(tetrahydropyran-2'-yl)oxy>-2-decynoate

Downstream raw materials:

2-hydroxy-6-[(8Z,11Z)-8,11-pentadecadienyl]benzoic acid

2-methoxy-6-pentadeca-8c,11c-dienyl-benzoic acid methyl ester

Refernces