(R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone

Base Information

• Chemical Name: (R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone
• CAS No.: 886537-67-3
• Molecular Formula: C₁₂H₁₈O₂
• Molecular Weight: 194.274
• Mol file: 886537-67-3.mol

Synonyms:(R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone

Chemical Property of (R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone

There total 1 articles about (R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone 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: 92.0%

(R)-Carvone (6485-40-1,2244-16-8) + acetaldehyde (75-07-0,9002-91-9) → (R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone (886537-67-3)

Guidance literature:

(R)-Carvone; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -15 - 0 ℃; for 5h;

acetaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1016/j.tet.2006.01.062

Reference yield: 90.0%

(R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone (886537-67-3) + oxalyl dichloride (79-37-8) → (5R)-6-acetyl-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone (886537-41-3)

Guidance literature:

With dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 20 ℃;

DOI:10.1016/j.tet.2006.01.062

Reference yield:

(R)-6-(1-Hydroxy-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone (886537-67-3) → 3-((1S,6S)-1-acetyl-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl)propanal (886537-43-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / DMSO; triethylamine / CH₂Cl₂ / -60 - 20 °C

2.1: NaH / tetrahydrofuran / 0 °C

2.2: 93 percent / Bu₄NHSO₄ / tetrahydrofuran; dimethylformamide / 12 h / 5 °C

3.1: 93 percent / pyridinium p-toluenesulsonate / H₂O; acetone / 1 h / Heating

With pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; 1.1: Swern oxidation;

DOI:10.1016/j.tet.2006.01.062

upstream raw materials:

(R)-Carvone

acetaldehyde

Downstream raw materials:

(5R)-6-acetyl-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

3-((1S,6S)-1-acetyl-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl)propanal

(5S,6S)-6-acetyl-2-methyl-6-((E)-4-methylhexa-3,5-dienyl)-5-(prop-1-en-2-yl)cyclohex-2-enone

(E)-5-((1S,6S)-1-acetyl-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl)-2-methylpent-2-enal