(2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate

Base Information

• Chemical Name: (2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate
• CAS No.: 332343-83-6
• Molecular Formula: C₃₂H₄₄O₂
• Molecular Weight: 460.7
• Mol file: 332343-83-6.mol

Synonyms:(2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate

Chemical Property of (2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate

There total 5 articles about (2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate 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:

benzoyl chloride (98-88-4) + (2E,4E,7E,11E,15E)-8,12,16,20-Tetramethyl-henicosa-2,4,7,11,15,19-hexaen-1-ol (332343-92-7) → (2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate (332343-83-6)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 23 ℃; for 2h;

DOI:10.1021/ja004043r

Reference yield:

Geranylgeraniol (24034-73-9) → (2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate (332343-83-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: CuCN / tetrahydrofuran / 1 h / -40 - 0 °C

2.2: 427 mg / tetrahydrofuran; hexane / 12 h / 0 °C

3.1: Cp₂ZrHCl / tetrahydrofuran / 0.75 h / 20 °C

3.2: 75 percent / ZnCl₂ / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

4.1: DIBAL-H / tetrahydrofuran; toluene / 0.67 h / -78 - 0 °C

4.2: MeOH; Na₂SO₄*10H₂O / tetrahydrofuran / 0.5 h / 23 °C

5.1: pyridine; 4-DMAP / CH₂Cl₂ / 2 h / 23 °C

With pyridine; dmap; Schwartz's reagent; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/ja004043r

Reference yield:

2E,6E,10E-geranylgeranyl methanesulfonate (71668-80-9) → (2E,4E,7E,11E,15E)-8,12,16,20-tetramethylheneicosa-2,4,7,11,15,19-hexaenyl benzoate (332343-83-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: CuCN / tetrahydrofuran / 1 h / -40 - 0 °C

1.2: 427 mg / tetrahydrofuran; hexane / 12 h / 0 °C

2.1: Cp₂ZrHCl / tetrahydrofuran / 0.75 h / 20 °C

2.2: 75 percent / ZnCl₂ / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

3.1: DIBAL-H / tetrahydrofuran; toluene / 0.67 h / -78 - 0 °C

3.2: MeOH; Na₂SO₄*10H₂O / tetrahydrofuran / 0.5 h / 23 °C

4.1: pyridine; 4-DMAP / CH₂Cl₂ / 2 h / 23 °C

With pyridine; dmap; Schwartz's reagent; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja004043r

upstream raw materials:

benzoyl chloride

(2E,4E,7E,11E,15E)-8,12,16,20-Tetramethyl-henicosa-2,4,7,11,15,19-hexaen-1-ol

Geranylgeraniol

2E,6E,10E-geranylgeranyl methanesulfonate

Downstream raw materials:

[(1R,2S,5R)-1-Bromo-2-{[(2-methoxy-phenyl)-dimethyl-silanyl]-methyl}-5-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-cyclohex-3-enyl]-methanol

(1R,2S,5R)-1-Bromo-2-{[(2-methoxy-phenyl)-dimethyl-silanyl]-methyl}-5-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-cyclohex-3-enecarbaldehyde

(2-Methoxy-phenyl)-dimethyl-[(3S,4R,7R)-7-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-1-oxa-spiro[2.5]oct-5-en-4-ylmethyl]-silane

(1S,2S,5R)-1,2-Bis-hydroxymethyl-5-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-cyclohex-3-enol

Refernces