3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde

Base Information

• Chemical Name: 3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde
• CAS No.: 100414-95-7
• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.473
• Mol file: 100414-95-7.mol

Synonyms:3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde

Chemical Property of 3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde

There total 10 articles about 3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde 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: 21.0%

2,6,6-Trimethyl-5-(3,7-dimethylocta-2E,6-dienyl)-1-cyclohexene-1-carboxaldehyde (100414-94-6) → 3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde (100414-95-7)

Guidance literature:

With tert.-butylhydroperoxide; selenium(IV) oxide; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85602-7

Reference yield:

trans-geranyl bromide (6138-90-5) → 3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde (100414-95-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) LDA / 1.) THF, -78 deg C

2: 2.) aq HCl

3: 1.) lithium dimethylcuprate / 1.) -78 deg C

4: 58 percent / TiCl₄ / CH₂Cl₂

5: 98 percent

6: 1.) POCl₃, 2.) KOH / 1.) pyridine, 65 deg C, 1.5 h 2.) MeOH

7: t-BuO₂H / SeO₂ / CH₂Cl₂ / 3 h / 25 °C

With hydrogenchloride; tert.-butylhydroperoxide; potassium hydroxide; lithium dimethylcuprate; titanium tetrachloride; lithium diisopropyl amide; trichlorophosphate; selenium(IV) oxide; In dichloromethane;

DOI:10.1016/S0040-4039(00)98306-0

Reference yield:

4-(3,7-dimethylocta-2,6-dien-1-yl)-3-methylcyclohex-2-en-1-one (100414-90-2) → 3-(3,7-Dimethyl-8-hydroxy-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde (100414-95-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) lithium dimethylcuprate / 1.) -78 deg C

2: 58 percent / TiCl₄ / CH₂Cl₂

3: 98 percent

4: 1.) POCl₃, 2.) KOH / 1.) pyridine, 65 deg C, 1.5 h 2.) MeOH

5: t-BuO₂H / SeO₂ / CH₂Cl₂ / 3 h / 25 °C

With tert.-butylhydroperoxide; potassium hydroxide; lithium dimethylcuprate; titanium tetrachloride; trichlorophosphate; selenium(IV) oxide; In dichloromethane;

DOI:10.1016/S0040-4039(00)98306-0

upstream raw materials:

2,6,6-Trimethyl-5-(3,7-dimethylocta-2E,6-dienyl)-1-cyclohexene-1-carboxaldehyde

trans-geranyl bromide

4-(3,7-dimethylocta-2,6-dien-1-yl)-3-methylcyclohex-2-en-1-one

3,3-Dimethyl-4-(3,7-dimethylocta-2E,6-dienyl)-1-trimethylsilyloxy-1-cyclohexene

Downstream raw materials:

3-(3,7-Dimethyl-8-oxo-2E,6E-octadienyl)-2,2,6-trimethyl-1-cyclohexene-1-carboxaldehyde