1-methoxy-4-(1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene

Base Information

• Chemical Name: 1-methoxy-4-(1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene
• CAS No.: 852058-92-5
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355

Synonyms:

Chemical Property of 1-methoxy-4-(1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-methoxy-4-(1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene

There total 15 articles about 1-methoxy-4-(1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene 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:

4-(4-methoxyphenyl)-4,5,5-trimethylcyclopent-2-enone (807377-62-4) → 1-methoxy-4-(1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene (852058-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen / Pd/C / ethanol / 3 h / 20 °C

2: 95 mg / BF₃*OEt₂ / benzene / 12 h / 0 - 20 °C

3: Raney nickel / ethanol / 2 h / Heating

4: lithium; liq. ammonia / ethanol; tetrahydrofuran / 2.5 h

With boron trifluoride diethyl etherate; ammonia; hydrogen; lithium; nickel; palladium on activated charcoal; In tetrahydrofuran; ethanol; benzene; 4: Birch reduction;

DOI:10.1081/SCC-200034755

Reference yield:

2,2-dimethyl-4-pentenal (5497-67-6) → 1-methoxy-4-(1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene (852058-92-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 85 percent / lithium / tetrahydrofuran / 1 h / sonication

2.1: 97 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 3 h / 20 °C

3.1: magnesium / tetrahydrofuran

3.2: 70 percent / tetrahydrofuran / 4 h / 20 °C

4.1: 83 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 30 h / 20 °C

5.1: 70 percent / sodium borohydride / methanol / 2 h / cooling

6.1: 47 percent / propionic acid / 48 h / 180 °C

7.1: 98 percent / PhCH=RhCl₂(PCy₃)2 / CH₂Cl₂ / 4 h / 20 °C

8.1: hydrogen / Pd/C / ethanol / 3 h / 20 °C / 760 Torr

9.1: 84 mg / LiAlH₄ / diethyl ether / 0.75 h / 0 - 20 °C

10.1: pyridinium chlorochromate; silica gel / CH₂Cl₂ / 0.5 h / 20 °C

11.1: 14 mg / (PPh₃)3RhCl / benzene / 48 h / 120 - 130 °C

12.1: lithium; liq. ammonia / ethanol; tetrahydrofuran / 2.5 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; ammonia; hydrogen; silica gel; lithium; magnesium; propionic acid; pyridinium chlorochromate; palladium on activated charcoal; Wilkinson's catalyst; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene; 1.1: Barbier coupling / 6.1: Johnson-Claisen orthoester rearrangement / 12.1: Birch reduction;

DOI:10.1081/SCC-200034755

Reference yield:

1-(4-methoxyphenyl)-2,2-dimethylpent-4-en-1-ol (807376-14-3) → 1-methoxy-4-(1,2,2-trimethyl-cyclopentyl)-cyclohexa-1,4-diene (852058-92-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 97 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 3 h / 20 °C

2.1: magnesium / tetrahydrofuran

2.2: 70 percent / tetrahydrofuran / 4 h / 20 °C

3.1: 83 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 30 h / 20 °C

4.1: 70 percent / sodium borohydride / methanol / 2 h / cooling

5.1: 47 percent / propionic acid / 48 h / 180 °C

6.1: 98 percent / PhCH=RhCl₂(PCy₃)2 / CH₂Cl₂ / 4 h / 20 °C

7.1: hydrogen / Pd/C / ethanol / 3 h / 20 °C / 760 Torr

8.1: 84 mg / LiAlH₄ / diethyl ether / 0.75 h / 0 - 20 °C

9.1: pyridinium chlorochromate; silica gel / CH₂Cl₂ / 0.5 h / 20 °C

10.1: 14 mg / (PPh₃)3RhCl / benzene / 48 h / 120 - 130 °C

11.1: lithium; liq. ammonia / ethanol; tetrahydrofuran / 2.5 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; ammonia; hydrogen; silica gel; lithium; magnesium; propionic acid; pyridinium chlorochromate; palladium on activated charcoal; Wilkinson's catalyst; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene; 5.1: Johnson-Claisen orthoester rearrangement / 11.1: Birch reduction;

DOI:10.1081/SCC-200034755

upstream raw materials:

4-(1,2,2-trimethylcyclopentyl)anisole

2,2-dimethyl-4-pentenal

4-(4-methoxyphenyl)-4,5,5-trimethylcyclopent-2-enone

1-(4-methoxyphenyl)-2,2-dimethylpent-4-en-1-one

Downstream raw materials:

4-(1,2,2-trimethylcyclopentyl)cyclohex-3-enone

4-(1,2,2-trimethylcyclopentyl)cyclohex-2-enone

(+/-)-cuprenenol

neocuprenenol

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