3-Methyl-5-(2,2-dimethyl-6-methylen-cyclohexyl)-pent-2-enal

Base Information

• Chemical Name: 3-Methyl-5-(2,2-dimethyl-6-methylen-cyclohexyl)-pent-2-enal
• CAS No.: 68420-46-2
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355
• Mol file: 68420-46-2.mol

Synonyms:

Chemical Property of 3-Methyl-5-(2,2-dimethyl-6-methylen-cyclohexyl)-pent-2-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Methyl-5-(2,2-dimethyl-6-methylen-cyclohexyl)-pent-2-enal

There total 14 articles about 3-Methyl-5-(2,2-dimethyl-6-methylen-cyclohexyl)-pent-2-enal 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: 81.0%

Ethinyl-dihydro-γ-jonol (60290-61-1) → 3-Methyl-5-(2,2-dimethyl-6-methylen-cyclohexyl)-pent-2-enal (68420-46-2,68420-47-3)

Guidance literature:

With tris-(triphenylsiloxy)-vanadium oxide; triphenylhydroxysilane; In toluene; at 120 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/chem.201503403

Reference yield:

2-Benzenesulfinyl-3-(2,2-dimethyl-6-oxo-cyclohexyl)-propionic acid ethyl ester → (E)-5-(2,2-Dimethyl-6-methylene-cyclohexyl)-3-methyl-pent-2-enal (68420-46-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / RaNi / H₂O

2: 71 percent / TiCl₄, Zn

3: 98 percent / LiAlH₄

4: 96 percent / DMSO, ClCOCOCl, Et₃N

5: 100 percent

6: 98 percent / DMSO, ClCOCOCl, Et₃N

7: 100 percent

8: PCC

With lithium aluminium tetrahydride; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; zinc; In water;

DOI:10.1021/jo9610568

Reference yield:

methyl (+/-)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate (81752-87-6) → 3-Methyl-5-(2,2-dimethyl-6-methylen-cyclohexyl)-pent-2-enal (68420-46-2,68420-47-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 3 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 16 h / Inert atmosphere; Reflux

3.1: 1-triphenylphosphoranylidene-2-propanone; tri-n-butyl-tin hydride; ammonium chloride; water / tetrahydrofuran / 3 h / Inert atmosphere

3.2: 5 h / Inert atmosphere

4.1: tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.1: tris-(triphenylsiloxy)-vanadium oxide; triphenylhydroxysilane / toluene / 1.5 h / 120 °C / Inert atmosphere

With lithium aluminium tetrahydride; oxalyl dichloride; water; tri-n-butyl-tin hydride; tris-(triphenylsiloxy)-vanadium oxide; ammonium chloride; dimethyl sulfoxide; 1-triphenylphosphoranylidene-2-propanone; triphenylhydroxysilane; In tetrahydrofuran; dichloromethane; toluene; 5.1: |Meyer-Schuster Rearrangement;

DOI:10.1002/chem.201503403

upstream raw materials:

5-(6',6'-dimethyl-2'-methylenecyclohexyl)-3-hydroxy-3-methyl-pent-1-ene

4-(6',6'-dimethyl-2'-methylenecyclohexyl)butan-2-ol

4-(2',2'-Dimethyl-6'-methylidenecyclohexyl)butan-2-one

3-(2,2-dimethyl-6-oxo-cyclohexyl)-propionic acid ethyl ester

Refernces

• 1、 Engler,Ali,Takusagawa. "Studies on the synthesis of acanthodoral and nanaimoal: Evaluation of cationic cyclization routes". . p. 8456 - 8463. Retrieved 2007/10/03.