(R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone

Base Information

• Chemical Name: (R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone
• CAS No.: 69153-91-9
• Molecular Formula: C₁₁H₁₈O
• Molecular Weight: 166.263
• Mol file: 69153-91-9.mol

Synonyms:(R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone

Chemical Property of (R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone

There total 4 articles about (R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone 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: 17.0%

3,3,6,6-tetramethylbicyclo[3.1.1]heptan-2-one (36203-40-4) → (R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone (69153-91-9)

Guidance literature:

at 450 ℃;

DOI:10.1021/jo01300a006

Reference yield:

(2R,4R)-(-)-2-methyl-4-isopropenylcyclohexanone (118710-90-0) → (R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone (69153-91-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOMe, 2.) p-TsOH

2: 1.) t-BuOK, 2.) 25percent KOH / 1.) room temperature, 30 min, 2.) ethylene alcohol, reflux, 48 h

With potassium hydroxide; potassium tert-butylate; sodium methylate; toluene-4-sulfonic acid;

DOI:10.1021/ja00392a008

Reference yield:

(R)-(+)-2,2-Dimethyl-4-(2-bromo-2-propyl)cyclohexanone (73368-32-8) → (R)-(+)-2,2-Dimethyl-4-isopropenylcyclohexanone (69153-91-9)

Guidance literature:

With 3-ethylpentan-3-ol; potassium; at 60 ℃; for 14h; Yield given;

DOI:10.1021/jo01300a006

upstream raw materials:

3,3,6,6-tetramethylbicyclo[3.1.1]heptan-2-one

(R)-(+)-2,2-Dimethyl-4-(2-bromo-2-propyl)cyclohexanone

2-Methyl-4-isopropenyl-6-n-butylthiomethylen-cyclohexanon

methyl iodide

Downstream raw materials:

(R)-(+)-2,2-Dimethyl-4-(1-methyl-1-cyclopropyl)cyclohexanone

(1S,4R)-(+)-2,2-Dimethyl-4-tert-butylcyclohexan-1-ol

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,4R)-4-tert-butyl-2,2-dimethyl-cyclohexyl ester

(R)-(+)-2,2-Dimethyl-4-tert-butylcyclohexanone

Refernces

• 1、 Konopelski, Joseph P.,Djerassi, Carl. "Synthesis of Chiral Conformationally Fixed Cyclohexanones". . p. 2297 - 2301. Retrieved 2007/10/02.