Benzenepropanol, a-methyl-, 4-methylbenzenesulfonate, (S)-

Base Information

• Chemical Name: Benzenepropanol, a-methyl-, 4-methylbenzenesulfonate, (S)-
• CAS No.: 116199-39-4
• Molecular Formula: C17H20O3S
• Molecular Weight: 304.41
• Mol file: 116199-39-4.mol

Synonyms:

Chemical Property of Benzenepropanol, a-methyl-, 4-methylbenzenesulfonate, (S)-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenepropanol, a-methyl-, 4-methylbenzenesulfonate, (S)-

There total 4 articles about Benzenepropanol, a-methyl-, 4-methylbenzenesulfonate, (S)- 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: 100.0%

(+)-(S)-4-phenylbutan-2-ol (2344-70-9,14786-43-7,39516-03-5,22148-86-3) + p-toluenesulfonyl chloride (98-59-9) → (S)-4-phenylbutan-2-yl 4-methylbenzenesulfonate (116199-39-4)

Guidance literature:

With trimethylamine hydrochloride; triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.7b07983

Reference yield: 95.32%

1-phenyl-3-butanol (2344-70-9) + p-toluenesulfonyl chloride (98-59-9) → 4-phenylbutan-2-yl 4-methylbenzene-1-sulfonate (116199-39-4,116199-40-7,52134-15-3)

Guidance literature:

With triethylamine; In dichloromethane; at -10 - 20 ℃;

Reference yield:

benzylmagnesium chloride (6921-34-2) → (S)-4-phenylbutan-2-yl 4-methylbenzenesulfonate (116199-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(l) iodide / tetrahydrofuran / 0.08 h / -30 °C / Inert atmosphere

1.2: 2.5 h / -30 - 0 °C / Inert atmosphere

2.1: triethylamine; trimethylamine hydrochloride / dichloromethane / 1 h / 0 °C / Inert atmosphere

With copper(l) iodide; trimethylamine hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.201905173

upstream raw materials:

1-phenyl-3-butanol

p-toluenesulfonyl chloride

(+)-(S)-4-phenylbutan-2-ol

benzylmagnesium chloride

Downstream raw materials:

(R)-(3-cyclohexylbutyl)benzene

(3-cyclohexylbutyl)benzene

Refernces

• 1、 Alexanian, Erik J.,Tercenio, Quentin D.. "Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles". supporting information. p. 7215 - 7219. Retrieved 2021/09/22.
• 2、 Bode, Bela E.,Chabbra, Sonia,Champion, Sue,Dawson, Daniel M.,Sood, D. Eilidh,Sutherland, Andrew,Watson, Allan J. B.. "Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group". supporting information. p. 8460 - 8463. Retrieved 2020/04/10.