6-(3-Methoxybutylidene)-1,5,5-trimethylcyclohex-1-ene

Base Information

• Chemical Name: 6-(3-Methoxybutylidene)-1,5,5-trimethylcyclohex-1-ene
• CAS No.: 945426-65-3
• Molecular Formula: C14H24O
• Molecular Weight: 208.344
• Hs Code.: 2909209000
• DSSTox Substance ID: DTXSID80699512
• Mol file: 945426-65-3.mol

Synonyms:6-(3-methoxybutylidene)-1,5,5-trimethylcyclohexene;RETRO-METHYL-ALPHA-IONOL;6-(3-Methoxybutylidene)-1,5,5-trimethylcyclohex-1-ene;DTXSID80699512;FT-0671231

Chemical Property of 6-(3-Methoxybutylidene)-1,5,5-trimethylcyclohex-1-ene

Chemical Property:

• Vapor Pressure: 0.0185mmHg at 25°C
• Boiling Point: 261.7°C at 760 mmHg
• Flash Point: 98.8°C
• PSA: 0.00000
• Density: 0.907g/cm³
• LogP: 4.13580
• Solubility.: Chloroform
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 208.182715385
• Heavy Atom Count: 15
• Complexity: 271

Purity/Quality:

97% ^*data from raw suppliers

retro-Methyl-α-ionol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CCCC(C1=CCC(C)OC)(C)C
• Uses: An intermediate for synthesizing ?Damascenone. An intermediate for synthesizing β-Damascenone.

Technology Process of 6-(3-Methoxybutylidene)-1,5,5-trimethylcyclohex-1-ene

There total 2 articles about 6-(3-Methoxybutylidene)-1,5,5-trimethylcyclohex-1-ene 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: 96.0%

(Z)-4-(2,6,6-trimethylcyclohex-2-enylidene)butan-2-ol (55093-47-5) + methyl iodide (74-88-4) → 4-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2-methoxybutane (945426-65-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1080/00397910701196546

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → 4-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2-methoxybutane (945426-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isopropenyl acetate; p-toluenesulfonic acid monohydrate / 24 h / Heating

1.2: NaBH₄ / aq. ethanol / 1.5 h / Heating

2.1: 96 percent / sodium hydride / dimethylformamide / 0 - 20 °C

With Isopropenyl acetate; sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1080/00397910701196546

Reference yield:

4-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2-methoxybutane (945426-65-3) → Damascenon (23726-93-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH₂Cl₂ / 8 h / 20 °C

1.2: 220 mg / sulfuric acid / H₂O; diethyl ether / 6 h / 20 °C

2.1: pyridine / diethyl ether / 0 - 20 °C

3.1: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 20 °C

4.1: 78 percent / active neutral alumina / diethyl ether / 12 h / 20 °C

5.1: p-toluenesulfonic acid / benzene / 12 h / 50 °C

With pyridine; aluminum oxide; sodium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In diethyl ether; dichloromethane; benzene;

DOI:10.1080/00397910701196546

upstream raw materials:

(Z)-4-(2,6,6-trimethylcyclohex-2-enylidene)butan-2-ol

methyl iodide

(E)-β-ionone

Downstream raw materials:

C₁₄H₂₆O₃

C₁₄H₂₄O₂

C₁₆H₂₈O₄

C₁₆H₂₆O₄