4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone

Base Information

• Chemical Name: 4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone
• CAS No.: 72049-77-5
• Molecular Formula: C₂₀H₂₈O₃S
• Molecular Weight: 348.507
• Mol file: 72049-77-5.mol

Synonyms:

Chemical Property of 4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone

There total 9 articles about 4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone 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:

Nerol (106-25-2) → 4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone (72049-77-5,72049-78-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) PBr₃ / 1. ether, 3 h, room temp.; 2. DMF,20 h , room temp.

2: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 7 h / Ambient temperature

3: formic acid / 2 h / 100 °C

4: 85 percent / tetrahydrofuran; diethyl ether / 5 - 10 °C

5: 2 percent / SnCl₄ / CH₂Cl₂ / 30 h / 35 °C

6: 1) BuLi / 1. -50 grad C, 30 min, THF; 2. -50 grad C, then 20 h room temp.

7: pyridinium chlorochromate / CH₂Cl₂ / 8 h / Ambient temperature

With n-butyllithium; formic acid; phosphorus tribromide; tin(IV) chloride; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo01289a003

Reference yield:

(Z)-(3,7-dimethylocta-2,6-diene-1-sulfonyl)benzene (56881-52-8) → 4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone (72049-77-5,72049-78-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 7 h / Ambient temperature

2: formic acid / 2 h / 100 °C

3: 85 percent / tetrahydrofuran; diethyl ether / 5 - 10 °C

4: 2 percent / SnCl₄ / CH₂Cl₂ / 30 h / 35 °C

5: 1) BuLi / 1. -50 grad C, 30 min, THF; 2. -50 grad C, then 20 h room temp.

6: pyridinium chlorochromate / CH₂Cl₂ / 8 h / Ambient temperature

With n-butyllithium; formic acid; tin(IV) chloride; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo01289a003

Reference yield:

sodium benzenesulfonate (873-55-2) → 4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone (72049-77-5,72049-78-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) PBr₃ / 1. ether, 3 h, room temp.; 2. DMF,20 h , room temp.

2: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 7 h / Ambient temperature

3: formic acid / 2 h / 100 °C

4: 85 percent / tetrahydrofuran; diethyl ether / 5 - 10 °C

5: 2 percent / SnCl₄ / CH₂Cl₂ / 30 h / 35 °C

6: 1) BuLi / 1. -50 grad C, 30 min, THF; 2. -50 grad C, then 20 h room temp.

7: pyridinium chlorochromate / CH₂Cl₂ / 8 h / Ambient temperature

With n-butyllithium; formic acid; phosphorus tribromide; tin(IV) chloride; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo01289a003

upstream raw materials:

Nerol

(Z)-(3,7-dimethylocta-2,6-diene-1-sulfonyl)benzene

sodium benzenesulfonate

2,5,6,6-Tetramethyl-1-<(phenylsulfonyl)methyl>cyclohexene

Downstream raw materials:

beta-irone