Cyclopentanecarboxaldehyde, 1-(2-methoxy-5-methylphenyl)-2,2-dimethyl-

Base Information

• Chemical Name: Cyclopentanecarboxaldehyde, 1-(2-methoxy-5-methylphenyl)-2,2-dimethyl-
• CAS No.: 603985-12-2
• Molecular Formula: C16H22O2
• Molecular Weight: 246.349
• Mol file: 603985-12-2.mol

Synonyms:

Chemical Property of Cyclopentanecarboxaldehyde, 1-(2-methoxy-5-methylphenyl)-2,2-dimethyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopentanecarboxaldehyde, 1-(2-methoxy-5-methylphenyl)-2,2-dimethyl-

There total 22 articles about Cyclopentanecarboxaldehyde, 1-(2-methoxy-5-methylphenyl)-2,2-dimethyl- 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: 90.0%

[1-(2'-methoxy-5'-methylphenyl)-2,2-dimethylcyclopentyl]-methanol (815620-64-5) → 1-(2-methoxy-5-methyl-phenyl)-2,2-dimethyl-cyclopentanecarbaldehyde (603985-12-2)

Guidance literature:

With silica gel; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1055/s-2005-865223

Reference yield:

2-(2-methoxy-5-methyl-phenyl)-pent-4-enoic acid (858128-74-2) → 1-(2-methoxy-5-methyl-phenyl)-2,2-dimethyl-cyclopentanecarbaldehyde (603985-12-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / DCC; DMAP / CH₂Cl₂ / 4 h / 20 °C

2.1: LDA / tetrahydrofuran

2.2: 77 percent / Et₃N / tetrahydrofuran / 5.5 h / -70 - 20 °C

3.1: Et₃N / tetrahydrofuran / 2 h / Heating

3.2: aq. HCl / tetrahydrofuran / 0.67 h

4.1: diethyl ether / 0.5 h / 0 °C

5.1: 98 percent / [Cl₂Ru(PCy₃)2=CHPh] / CH₂Cl₂ / 5 h / 20 °C

6.1: 100 percent / H₂ / Pd/C / ethanol / 5 h / 760 Torr

7.1: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

8.1: 90 percent / PCC; silica gel / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; lithium aluminium tetrahydride; hydrogen; silica gel; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 3.1: Ireland ester Claisen rearrangement;

DOI:10.1055/s-2005-865223

Reference yield:

methyl 2,2-dimethyl-1-(2-methoxy-5-methylphenyl)cyclopent-3-enecarboxylate (858128-77-5) → 1-(2-methoxy-5-methyl-phenyl)-2,2-dimethyl-cyclopentanecarbaldehyde (603985-12-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂ / Pd/C / ethanol / 5 h / 760 Torr

2: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

3: 90 percent / PCC; silica gel / CH₂Cl₂ / 0.5 h / 20 °C

With lithium aluminium tetrahydride; hydrogen; silica gel; pyridinium chlorochromate; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane;

DOI:10.1055/s-2005-865223

upstream raw materials:

1-[1-(2-methoxy-5-methyl-phenyl)-2,2-dimethyl-cyclopentyl]-2-methyl-propan-2-ol

[1-(2'-methoxy-5'-methylphenyl)-2,2-dimethylcyclopentyl]-methanol

2-(2-methoxy-5-methyl-phenyl)-pent-4-enoic acid

methyl 2,2-dimethyl-1-(2-methoxy-5-methylphenyl)cyclopent-3-enecarboxylate

Downstream raw materials:

methyl 1-(2-methoxy-5-methylphenyl)-2,2-dimethylcyclopentane-carboxylate

1-methoxy-4-methyl-2-(1,2,2-trimethylcyclopentyl)-benzene